Product Name

  • Name

    Boceprevir

  • EINECS 800-043-2
  • CAS No. 394730-60-0
  • Density 1.162 g/cm3
  • Solubility
  • Melting Point
  • Formula C27H45N5O5
  • Boiling Point
  • Molecular Weight 519.685
  • Flash Point
  • Transport Information
  • Appearance white powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 394730-60-0 (Boceprevir)
  • Hazard Symbols
  • Synonyms (1R,2S,5S)-N-(4-Amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[(2S)-2-(t
  • PSA 150.70000
  • LogP 3.52210

Synthetic route

(1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide
394735-28-5

(1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Stage #1: (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide With sodium hypochlorite solution; sodium acetate; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In tert-butyl methyl ether at 10 - 20℃;
Stage #2: With water; acetic acid In tert-butyl methyl ether for 2.25h;
Stage #3: With sodium hypochlorite solution; ascorbic acid Product distribution / selectivity; more than 3 stages;		94%
With sodium permanganate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; acetic acid In tert-butyl methyl ether; water at 12℃;91%
With Dess-Martin periodane In ethyl acetate at 5 - 18℃; for 5.25h; Reagent/catalyst;40%
C27H46N5O8S(1-)*Na(1+)
817170-37-9

C27H46N5O8S(1-)*Na(1+)

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
With Oxone In tert-butyl methyl ether; water at 25℃; for 1h; Purification / work up;94%
With dipotassium peroxodisulfate In tert-butyl methyl ether; water at 25℃; for 0.75h; Purification / work up;88%
With sodium chloride In tert-butyl methyl ether; water at 30℃; for 0.5h; Purification / work up;84%
With Glyoxilic acid In water at 8 - 25℃; for 4h; Purification / work up;65%
With sodium glyoxylate In water at 8 - 25℃; for 4.33333h; Purification / work up;52%
(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
816444-90-3

(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

C8H14N2O2*ClH
817169-86-1

C8H14N2O2*ClH

A

boceprevir
394730-60-0

boceprevir

B

N-methylmorpholine hydrochloride
3651-67-0

N-methylmorpholine hydrochloride

Conditions
ConditionsYield
With 4-methyl-morpholine; isobutyl chloroformate In ethyl acetate at 0 - 10℃; for 1h;A 90%
B n/a
...Expand
(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
816444-90-3

(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

C8H14N2O2*ClH
817169-86-1

C8H14N2O2*ClH

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 15 - 20℃; for 1h;85%
(2-cyclobutyl-1-formylethyl)carbamic acid tert-butyl ester
394735-19-4

(2-cyclobutyl-1-formylethyl)carbamic acid tert-butyl ester

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Et3N / CH2Cl2 / 12 h / 20 °C
2: H2O2; LiOH / methanol / 3 h / 0 °C
3: HCl / dioxane / 2 h / 20 °C
4: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
5: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1: Et3N / CH2Cl2 / 12 h / 20 °C
2: HCl / 24 h / Heating
3: Et3N / CH2Cl2 / 20 °C
4: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
5: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
6: HCl / dioxane / 2 h / 20 °C
7: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
8: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
(2-cyano-1-cyclobutylmethyl-2-hydroxyethyl)carbamic acid tert-butyl ester
394735-20-7

(2-cyano-1-cyclobutylmethyl-2-hydroxyethyl)carbamic acid tert-butyl ester

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2O2; LiOH / methanol / 3 h / 0 °C
2: HCl / dioxane / 2 h / 20 °C
3: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
4: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1: HCl / 24 h / Heating
2: Et3N / CH2Cl2 / 20 °C
3: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
4: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
5: HCl / dioxane / 2 h / 20 °C
6: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
7: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid
565456-75-9

2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
2: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
3: Et3N / CH2Cl2 / 12 h / 20 °C
4: H2O2; LiOH / methanol / 3 h / 0 °C
5: HCl / dioxane / 2 h / 20 °C
6: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
7: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
2: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
3: Et3N / CH2Cl2 / 12 h / 20 °C
4: HCl / 24 h / Heating
5: Et3N / CH2Cl2 / 20 °C
6: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
7: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
8: HCl / dioxane / 2 h / 20 °C
9: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
10: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
tert-butyl 3-cyclobutyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate
394735-18-3

tert-butyl 3-cyclobutyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
2: Et3N / CH2Cl2 / 12 h / 20 °C
3: H2O2; LiOH / methanol / 3 h / 0 °C
4: HCl / dioxane / 2 h / 20 °C
5: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
6: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
2: Et3N / CH2Cl2 / 12 h / 20 °C
3: HCl / 24 h / Heating
4: Et3N / CH2Cl2 / 20 °C
5: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
6: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
7: HCl / dioxane / 2 h / 20 °C
8: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
9: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
methyl 3-tert-butoxycarbonylamino-4-cyclobutyl-2-hydroxybutyrate
394735-21-8

methyl 3-tert-butoxycarbonylamino-4-cyclobutyl-2-hydroxybutyrate

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
2: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
3: HCl / dioxane / 2 h / 20 °C
4: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
5: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
3-(tert-butoxycarbonylamino)-4-cyclobutyl-2-hydroxybutanoic acid
864765-28-6

3-(tert-butoxycarbonylamino)-4-cyclobutyl-2-hydroxybutanoic acid

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
2: HCl / dioxane / 2 h / 20 °C
3: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
4: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
ethyl 2-amino-3-cyclobutylpropanoate
394735-17-2

ethyl 2-amino-3-cyclobutylpropanoate

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: CH2Cl2 / 12 h / 20 °C
2: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
3: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
4: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
5: Et3N / CH2Cl2 / 12 h / 20 °C
6: H2O2; LiOH / methanol / 3 h / 0 °C
7: HCl / dioxane / 2 h / 20 °C
8: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
9: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1: CH2Cl2 / 12 h / 20 °C
2: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
3: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
4: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
5: Et3N / CH2Cl2 / 12 h / 20 °C
6: HCl / 24 h / Heating
7: Et3N / CH2Cl2 / 20 °C
8: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
9: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
10: HCl / dioxane / 2 h / 20 °C
11: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
12: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
3-(tert-butyl) 2-methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate
569679-06-7

3-(tert-butyl) 2-methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: HCl / dioxane
2: BOP; N-methylmorpholine / CH2Cl2; dimethylformamide / 24 h / 20 °C
3: HCl / dioxane / 3 h / 20 °C
4: CH2Cl2 / 20 °C
5: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
6: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
7: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
ethyl 2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoate
816430-02-1

ethyl 2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoate

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
2: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
3: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
4: Et3N / CH2Cl2 / 12 h / 20 °C
5: H2O2; LiOH / methanol / 3 h / 0 °C
6: HCl / dioxane / 2 h / 20 °C
7: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
8: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
2: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
3: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
4: Et3N / CH2Cl2 / 12 h / 20 °C
5: HCl / 24 h / Heating
6: Et3N / CH2Cl2 / 20 °C
7: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
8: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
9: HCl / dioxane / 2 h / 20 °C
10: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
11: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
tert-butyl 4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-ylcarbamate
394735-22-9

tert-butyl 4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-ylcarbamate

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HCl / dioxane / 2 h / 20 °C
2: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
3: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / isopropyl alcohol / 4 h / 50 °C / Large scale
2: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; ethyl acetate; 1-methyl-pyrrolidin-2-one / 16 h / 20 - 24 °C
3: acetic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium permanganate / tert-butyl methyl ether; water / 12 °C
View Scheme
2-(benzhydrylidene-amino)-3-cyclobutyl-propionic acid ethyl ester
1025799-39-6

2-(benzhydrylidene-amino)-3-cyclobutyl-propionic acid ethyl ester

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 18 g / aq. HCl / diethyl ether / 5 h / 20 °C
2: CH2Cl2 / 12 h / 20 °C
3: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
4: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
5: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
6: Et3N / CH2Cl2 / 12 h / 20 °C
7: H2O2; LiOH / methanol / 3 h / 0 °C
8: HCl / dioxane / 2 h / 20 °C
9: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
10: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 13 steps
1: 18 g / aq. HCl / diethyl ether / 5 h / 20 °C
2: CH2Cl2 / 12 h / 20 °C
3: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
4: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
5: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
6: Et3N / CH2Cl2 / 12 h / 20 °C
7: HCl / 24 h / Heating
8: Et3N / CH2Cl2 / 20 °C
9: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
10: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
11: HCl / dioxane / 2 h / 20 °C
12: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
13: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
(1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyryl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester
394735-26-3

(1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyryl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: HCl / dioxane / 3 h / 20 °C
2: CH2Cl2 / 20 °C
3: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
4: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
5: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride

methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: BOP; N-methylmorpholine / CH2Cl2; dimethylformamide / 24 h / 20 °C
2: HCl / dioxane / 3 h / 20 °C
3: CH2Cl2 / 20 °C
4: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
5: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
6: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 0.17 h / 0 - 5 °C
1.2: 6 h / 25 - 30 °C
2.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 6 h / 25 - 30 °C
3.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 5 h / 0 - 30 °C
4.1: Dess-Martin periodane / dichloromethane / 0 - 30 °C
View Scheme
methyl (1R,2S,5S)-3-((S)-2-(3-(tert-butyl)-ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate
394735-27-4

methyl (1R,2S,5S)-3-((S)-2-(3-(tert-butyl)-ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
2: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
3: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: water; lithium hydroxide monohydrate / tetrahydrofuran / 6 h / 25 - 30 °C
2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 5 h / 0 - 30 °C
3: Dess-Martin periodane / dichloromethane / 0 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: water; sodium hydroxide / toluene; methanol / 0 - 30 °C
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / N,N-dimethyl-formamide; ethyl acetate / 0 - 10 °C
3: Dess-Martin periodane / ethyl acetate / 5.25 h / 5 - 18 °C
View Scheme
methyl 3-amino-4-cyclobutyl-2-hydroxybutyrate hydrochloride

methyl 3-amino-4-cyclobutyl-2-hydroxybutyrate hydrochloride

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N / CH2Cl2 / 20 °C
2: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
3: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
4: HCl / dioxane / 2 h / 20 °C
5: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
6: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride

3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
2: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; ethyl acetate; 1-methyl-pyrrolidin-2-one / 16 h / 20 - 24 °C
2: acetic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium permanganate / tert-butyl methyl ether; water / 12 °C
View Scheme
(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
816444-90-3

(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
2: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 5 h / 0 - 30 °C
2: Dess-Martin periodane / dichloromethane / 0 - 30 °C
View Scheme
(1R,2S,5S)-methyl 3-((S)-2-amino-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride

(1R,2S,5S)-methyl 3-((S)-2-amino-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: CH2Cl2 / 20 °C
2: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
3: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
4: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
(Bromomethyl)cyclobutane
17247-58-4

(Bromomethyl)cyclobutane

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: t-BuOK / tetrahydrofuran / 1 h / 0 °C
1.2: tetrahydrofuran / 48 h / 20 °C
2.1: 18 g / aq. HCl / diethyl ether / 5 h / 20 °C
3.1: CH2Cl2 / 12 h / 20 °C
4.1: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
5.1: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
6.1: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
7.1: Et3N / CH2Cl2 / 12 h / 20 °C
8.1: H2O2; LiOH / methanol / 3 h / 0 °C
9.1: HCl / dioxane / 2 h / 20 °C
10.1: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
11.1: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: t-BuOK / tetrahydrofuran / 1 h / 0 °C
1.2: tetrahydrofuran / 48 h / 20 °C
2.1: 18 g / aq. HCl / diethyl ether / 5 h / 20 °C
3.1: CH2Cl2 / 12 h / 20 °C
4.1: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
5.1: 15.0 g / BOP; N-methylmorpholine / CH2Cl2 / 16 h / 20 °C
6.1: 14 g / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
7.1: Et3N / CH2Cl2 / 12 h / 20 °C
8.1: HCl / 24 h / Heating
9.1: Et3N / CH2Cl2 / 20 °C
10.1: LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
11.1: NH4Cl; EDCI; HOOBt / NMM / CH2Cl2; dimethylformamide / 72 h / 20 °C
12.1: HCl / dioxane / 2 h / 20 °C
13.1: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
14.1: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one
134107-65-6

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: BuLi / tetrahydrofuran
1.2: tetrahydrofuran / -78 - 20 °C
2.1: LiAlH4 / tetrahydrofuran / Heating
3.1: H2 / Pd/C
4.1: acetone / 3 h / -5 °C
5.1: toluene; methanol
6.1: HCl / dioxane
7.1: BOP; N-methylmorpholine / CH2Cl2; dimethylformamide / 24 h / 20 °C
8.1: HCl / dioxane / 3 h / 20 °C
9.1: CH2Cl2 / 20 °C
10.1: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
11.1: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
12.1: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one
103201-79-2

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: KHMDS; PhSeCl / -78 - 20 °C
1.2: H2O2; pyridine
2.1: BuLi / tetrahydrofuran
2.2: tetrahydrofuran / -78 - 20 °C
3.1: LiAlH4 / tetrahydrofuran / Heating
4.1: H2 / Pd/C
5.1: acetone / 3 h / -5 °C
6.1: toluene; methanol
7.1: HCl / dioxane
8.1: BOP; N-methylmorpholine / CH2Cl2; dimethylformamide / 24 h / 20 °C
9.1: HCl / dioxane / 3 h / 20 °C
10.1: CH2Cl2 / 20 °C
11.1: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
12.1: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
13.1: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
((1R,2S,5S)-3-Benzyl-6,6-dimethyl-3-aza-bicyclo[3.1.0]hex-2-yl)-methanol
1026427-11-1

((1R,2S,5S)-3-Benzyl-6,6-dimethyl-3-aza-bicyclo[3.1.0]hex-2-yl)-methanol

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: H2 / Pd/C
2: acetone / 3 h / -5 °C
3: toluene; methanol
4: HCl / dioxane
5: BOP; N-methylmorpholine / CH2Cl2; dimethylformamide / 24 h / 20 °C
6: HCl / dioxane / 3 h / 20 °C
7: CH2Cl2 / 20 °C
8: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
9: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
10: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
tert-butyl (1R,2S,5S)-2-(hydroxymethyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-3-carboxylate
219754-00-4

tert-butyl (1R,2S,5S)-2-(hydroxymethyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-3-carboxylate

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: acetone / 3 h / -5 °C
2: toluene; methanol
3: HCl / dioxane
4: BOP; N-methylmorpholine / CH2Cl2; dimethylformamide / 24 h / 20 °C
5: HCl / dioxane / 3 h / 20 °C
6: CH2Cl2 / 20 °C
7: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
8: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
9: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
(1R,2S,5S)-3-(tert-butoxycarbonyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
219754-02-6

(1R,2S,5S)-3-(tert-butoxycarbonyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: toluene; methanol
2: HCl / dioxane
3: BOP; N-methylmorpholine / CH2Cl2; dimethylformamide / 24 h / 20 °C
4: HCl / dioxane / 3 h / 20 °C
5: CH2Cl2 / 20 °C
6: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
7: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
8: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 0 - 30 °C
2: hydrogenchloride / isopropyl alcohol / 6 h / 60 - 65 °C
3: N-ethyl-N,N-diisopropylamine; HATU / acetonitrile / 5 h / 25 - 30 °C
4: Dess-Martin periodane / dichloromethane / 0 - 30 °C
View Scheme
(1S,2S,4S,7R)-6-aza-3,3-dimethyl-8-oxa-7-phenyltricyclo<4.3.0.0>nonan-5-one
219753-99-8

(1S,2S,4S,7R)-6-aza-3,3-dimethyl-8-oxa-7-phenyltricyclo<4.3.0.0>nonan-5-one

boceprevir
394730-60-0

boceprevir

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: LiAlH4 / tetrahydrofuran / Heating
2: H2 / Pd/C
3: acetone / 3 h / -5 °C
4: toluene; methanol
5: HCl / dioxane
6: BOP; N-methylmorpholine / CH2Cl2; dimethylformamide / 24 h / 20 °C
7: HCl / dioxane / 3 h / 20 °C
8: CH2Cl2 / 20 °C
9: LiOH*H2O / tetrahydrofuran; H2O / 3 h / 20 °C
10: EDCI; HOOBt; N-methylmorpholine / dimethylformamide; CH2Cl2 / 48 h / -20 °C
11: dichloroacetic acid; EDCI; DMSO / toluene / 4 h / 20 °C
View Scheme

Boceprevir Specification

The CAS registry number of Boceprevir is 394730-60-0. The systematic name is (1R,2S,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[N-(tert-butylcarbamoyl)-3-methyl-L-valyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide. In addition, the molecular formula is C27H45N5O5 and the molecular weight is 519.68. It should be stored in a cool and dry place. And it is a protease inhibitor used as a treatment for hepatitis C genotype 1. In addition, it belongs to the class of APIs.

Physical properties about Boceprevir are: (1)ACD/LogP: 2.05; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 2.05; (4)ACD/LogD (pH 7.4): 2.05; (5)ACD/BCF (pH 5.5): 21.32; (6)ACD/BCF (pH 7.4): 21.32; (7)ACD/KOC (pH 5.5): 310.81; (8)ACD/KOC (pH 7.4): 310.81; (9)#H bond acceptors: 10; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 101.55 Å2; (13)Index of Refraction: 1.533; (14)Molar Refractivity: 138.72 cm3; (15)Molar Volume: 446.8 cm3; (16)Polarizability: 54.99×10-24cm3; (17)Surface Tension: 46.4 dyne/cm; (18)Density: 1.162 g/cm3.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N3[C@H](C(=O)NC(C(=O)C(=O)N)CC1CCC1)[C@H]2C(C)([C@H]2C3)C)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C
(2)InChI: InChI=1/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1
(3)InChIKey: LHHCSNFAOIFYRV-DOVBMPENBP

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