Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; water at 20℃; for 12h; | 100% |
Stage #1: glycine With sodium hydroxide In 1,4-dioxane; water at 0℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃; | 100% |
With sodium hydroxide In 1,4-dioxane | 100% |
2-oxo-2-phenylethyl 2-(tert-butoxycarbonylamino)acetate
A
BOC-glycine
B
acetophenone
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethyl-o-phenylenediamine In acetonitrile for 2h; Irradiation; | A 100% B n/a |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal for 3h; | A 100% B n/a |
A
BOC-glycine
B
C16H10O3S
Conditions | Yield |
---|---|
In chloroform-d1 for 0.25h; Solvent; Photolysis; Inert atmosphere; | A 97% B n/a |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 20℃; for 8h; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 25℃; for 12h; | 94% |
(N-hydroxy-5-norbornene-2,3-diformylimino)tert-butyl ester
glycine
BOC-glycine
Conditions | Yield |
---|---|
With tertiary amine In 1,4-dioxane; water for 3h; | 85% |
tert-butyl 4,6-dimethoxy-1,3,5-triazinyl carbonate
glycine
BOC-glycine
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 0.5h; | 85% |
4-nitrobenzyl N-(tert-butoxycarbonyl)glycinate
BOC-glycine
Conditions | Yield |
---|---|
With sodium dithionite; sodium carbonate In acetonitrile | 80% |
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water for 0.166667h; Ambient temperature; | 80% |
2-oxo-2-phenylethyl 2-(tert-butoxycarbonylamino)acetate
A
BOC-glycine
B
(tert-butoxycarbonyl)glycine hydrazide
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol Product distribution; | A 75% B 12% |
N-Boc-glycine 2-(2-acetylphenyl)-1-methylethyl ester
BOC-glycine
Conditions | Yield |
---|---|
In acetonitrile for 3h; Photolysis; | 73% |
(E)-3-methoxyallyl 2-((tert-butoxycarbonyl)amino)acetate
BOC-glycine
Conditions | Yield |
---|---|
With zinc(II) chloride; lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 59% |
With potassium hexamethylsilazane; zinc(II) chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 54% |
tert-Butoxycarbonylamino-acetic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester
glycine ethyl ester hydrochloride
A
BOC-glycine
B
N-tert-butoxycarbonyl glycyl glycine methyl ester
Conditions | Yield |
---|---|
With 4-methyl-morpholine In N,N-dimethyl-formamide at 38℃; for 96h; | A n/a B 57% |
glycine ethyl ester hydrochloride
2,3,4,6-tetra-O-benzyl-1-O-(N-tert-butoxycarbonyl-glycyl)-β-D-glucopyranose
A
BOC-glycine
B
N-tert-butoxycarbonyl glycyl glycine methyl ester
2,3,4,6-tetra-O-benzyl-D-glucopyranose
Conditions | Yield |
---|---|
With 4-methyl-morpholine In N,N-dimethyl-formamide at 38℃; for 96h; | A n/a B 55% C n/a |
Conditions | Yield |
---|---|
With sodium carbonate In water; acetonitrile at -5 - 20℃; | 35% |
Glycine tert-butyl ester
2-oxo-2-phenylethyl 2-(tert-butoxycarbonylamino)acetate
A
BOC-glycine
B
Boc-glycylglycine tert-butyl ester
Conditions | Yield |
---|---|
In ethyl acetate for 24h; Product distribution; Ambient temperature; | A 10% B 30% |
Conditions | Yield |
---|---|
With sodium hydroxide; tert-butyl alcohol |
Conditions | Yield |
---|---|
With toluene Erwaermen des Reaktionsprodukts mit tert-Butylalkohol und anschliessenden Hydrolyse; |
Conditions | Yield |
---|---|
With triethylamine Behandeln des Reaktionsprodukts mit wss.NaOH und Dioxan; |
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
Stage #1: BOC-glycine; benzylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.0166667h; Stage #2: With HATU for 18h; | 100% |
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 99% |
With zirconium(IV) chloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Inert atmosphere; | 99% |
BOC-glycine
methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride
Nα-tert-butoxycarbonylglycyl-Nε-benzyloxycarbonyl-L-lysine methyl ester
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at -20 - 20℃; for 4h; Acylation; | 100% |
Stage #1: BOC-glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.5h; Cooling with ice; Stage #2: methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 92.2% |
(i) Et3N, ClCO2iBu, (ii) /BRN= 3578476/, Et3N; Multistep reaction; | |
With 4-methyl-morpholine; triethylamine; isobutyl chloroformate 1) THF, -10 deg C, 15 min, 2) THF, 12 h; Yield given. Multistep reaction; |
BOC-glycine
L-alanine benzyl ester p-toluenesulfonate
Boc-Gly-Ala-OBzl
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine | 100% |
With TEA; diphenyl phosphoryl azide In N,N-dimethyl-formamide 1.) 0 deg C, 4 h; 2.) r.t., overnight; | 85% |
Stage #1: BOC-glycine; L-alanine benzyl ester p-toluenesulfonate With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.166667h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere; |
BOC-glycine
benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride
(S)-1-(2-tert-butoxycarbonylaminoacetyl)pyrrolidine-2-carboxylic acid benzyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; triethylamine In chloroform | 100% |
With benzotriazol-1-ol; triethylamine In chloroform | 100% |
With benzotriazol-1-ol; triethylamine In chloroform | 100% |
BOC-glycine
L-valine benzyl ester p-toluenesulfonate salt
N-t-butoxycarbonylglycyl-L-valine benzyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine | 100% |
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere; | 94% |
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2.) overnight, 4 deg C; | 89% |
With 4-methyl-morpholine; isobutyl chloroformate 1.) THF, -15 deg C, 2.) DMF, a) -15 deg C, 30 min, b) r.t., 30 min.; Yield given. Multistep reaction; |
BOC-glycine
(-)-8-phenylmenthol
(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 13h; | 100% |
Stage #1: BOC-glycine With dmap; dicyclohexyl-carbodiimide In dichloromethane at -30℃; for 0.166667h; Stage #2: (-)-8-phenylmenthol In dichloromethane for 20h; Heating; | 96% |
With dmap; dicyclohexyl-carbodiimide | 93% |
BOC-glycine
2-(N-tert-butoxycarbonylamino)ethanol
Conditions | Yield |
---|---|
Stage #1: BOC-glycine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.25h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at -15℃; for 1h; | 100% |
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane for 4h; Ambient temperature; | 88% |
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at 0℃; for 2h; | 77.1% |
BOC-glycine
benzyl bromide
tert-butoxycarbonylamino-acetic acid benzyl ester
Conditions | Yield |
---|---|
Stage #1: BOC-glycine With caesium carbonate In methanol pH=7; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 5h; Further stages.; | 100% |
Stage #1: BOC-glycine With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0℃; for 18h; Further stages; | 100% |
With triethylamine In N,N-dimethyl-formamide at 25℃; for 5h; | 54% |
With caesium carbonate 1) MeOH, water, pH 7.0, 2) DMF, 5 h; Yield given. Multistep reaction; | |
With sodium iodide In acetone for 2h; Reflux; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: BOC-glycine; ethyl iodide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: In tetrahydrofuran at 0℃; | 100% |
Stage #1: BOC-glycine; ethyl iodide With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: With citric acid In water pH=2 - 3; | 100% |
Stage #1: BOC-glycine; ethyl iodide With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: With citric acid In water pH=2 - 3; | 100% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃; for 16h; | 100% |
With N-ethyl-N,N-diisopropylamine for 0.666667h; Reflux; | 91% |
With caesium carbonate In acetonitrile | 90% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 5h; | 100% |
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h; | 99% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 6h; | 96.9% |
BOC-glycine
isobutyl chloroformate
N-(t-butoxycarbonyl)glycyl i-butyl carbonate
Conditions | Yield |
---|---|
With 4-methyl-morpholine In tetrahydrofuran at -15℃; for 0.0833333h; | 100% |
With 4-methyl-morpholine In tetrahydrofuran at -20℃; for 0.05h; |
BOC-glycine
tetrakis-5,10,15,20-(o-aminophenyl)porphyrin
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 50h; Condensation; | 100% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Inert atmosphere; Cooling with ice; | 62% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane |
Conditions | Yield |
---|---|
Stage #1: H-Ala-Glu(OBzl)-OBzl hydrochloride With triethylamine In dichloromethane Hydrolysis; Stage #2: BOC-glycine With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 14h; Condensation; | 100% |
BOC-glycine
phenethylamine
tert-butyl N-{[(2-phenylethyl)carbamoyl]methyl}carbamate
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile at 0 - 20℃; Acylation; | 100% |
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃; for 72h; | 94% |
Stage #1: BOC-glycine With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Stage #2: phenethylamine In dichloromethane for 16h; | 81% |
Stage #1: BOC-glycine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: phenethylamine In N,N-dimethyl-formamide at 20℃; | 72% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 23℃; for 4h; Inert atmosphere; | 71% |
1-aza-18-crown-6
BOC-glycine
[2-oxo-2-(1,4,7,10,13-pentaoxa-16-aza-cyclooctadec-16-yl)-ethyl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With bis(trichloromethyl) carbonate; lutidine In tetrahydrofuran at 25 - 50℃; for 2h; | 100% |
With 2,6-dimethylpyridine; bis(trichloromethyl) carbonate In tetrahydrofuran Inert atmosphere; |
BOC-glycine
4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino}benzyl alcohol
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; | 100% |
BOC-glycine
4,6-O-di(tert-butyl)silanediyl-D-glucal
3-O-(N-tert-butoxycarbonyl-2'-amino-ethanoyl)-4,6-O-di-tert-butylsilanediyl-D-glucal
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane | 100% |
BOC-glycine
Propargylamine
tert-butyl (2-oxo-2-(prop-2-yn-1-ylamino)ethyl)carbamate
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h; Inert atmosphere; | 100% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; | 99% |
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In acetonitrile at 20℃; | 96% |
Conditions | Yield |
---|---|
Stage #1: BOC-glycine; anthranilic acid With pyridine; triphenyl phosphite at 150℃; for 0.166667h; microwave irradiation; Stage #2: 2-methoxyethylamine at 220℃; for 0.0666667h; microwave irradiation; | 100% |
Conditions | Yield |
---|---|
Stage #1: BOC-glycine; anthranilic acid With pyridine; triphenyl phosphite at 150℃; for 0.166667h; microwave irradiation; Stage #2: 2-methoxyethylamine at 180℃; for 0.05h; microwave irradiation; | 100% |
(3S,10R,16S)-16-{(1R)-3-[4-(hydroxymethyl)phenyl]-1-methylallyl}-3-isobutyl-10-(4-methoxybenzyl)-1-oxa-4,8,11-triazacyclohexadec-13-ene-2,5,9,12-tetraone
BOC-glycine
tert-butoxycarbonylamino-acetic acid 4-{3-[3-isobutyl-10-(4-methoxy-benzyl)-2,5,9,12-tetraoxo-1-oxa-4,8,11-triaza-cyclohexadec-13-en-16-yl]-but-1-enyl}-benzyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h; | 100% |
BOC-glycine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane for 3h; pH=9; | 100% |
BOC-glycine
2-(N-t-butoxycarbonylamino)thioacetamide
Conditions | Yield |
---|---|
With Lawessons reagent In dichloromethane at 25℃; for 16h; | 100% |
Stage #1: BOC-glycine With ammonium hydroxide; triethylamine; isobutyl chloroformate In tetrahydrofuran Stage #2: With tetraphosphorus decasulfide; sodium carbonate In tetrahydrofuran | 83% |
Multi-step reaction with 3 steps 1: Et3N / tetrahydrofuran / 0.42 h / -10 °C 2: aq. MH3 / tetrahydrofuran / 0.75 h / -10 °C 3: 85 percent / Lawesson's reagent / CH2Cl2 / 16 h / Ambient temperature View Scheme |
BOC-glycine
p-aminoiodobenzene
[(4-iodophenylcarbamoyl)methyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With dacarbazine; dmap In dichloromethane | 100% |
With dmap; diisopropyl-carbodiimide In dichloromethane for 20h; Inert atmosphere; | 100% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 5h; | 98% |
BOC-glycine
bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane | 100% |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; | 100% |
Molecular structure of Boc-glycine (CAS NO.4530-20-5) is:
Product Name: Boc-glycine
CAS Registry Number: 4530-20-5
IUPAC Name: 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
Molecular Weight: 175.18242 [g/mol]
Molecular Formula: C7H13NO4
XLogP3-AA: 0.5
H-Bond Donor: 2
H-Bond Acceptor: 4
EINECS: 224-864-5
Melting Point: 86-89 °C(lit.)
Water Solubility: soluble
Surface Tension: 40.1 dyne/cm
Density: 1.159 g/cm3
Flash Point: 144.9 °C
Enthalpy of Vaporization: 61.27 kJ/mol
Boiling Point: 315.9 °C at 760 mmHg
Vapour Pressure: 9.08E-05 mmHg at 25°C
Product Categories: Protected Amino Acids;Aminoacids Derivatives;Amino Acid Derivatives;Protected Amino Acid & Peptides;Amino Acids;Glycine [Gly, G];Boc-Amino Acids and Derivative;Amino Acids 13C, 2H, 15N;Absolute Configuration Determination (Exciton Chirality CD Method);Amino Acids (N-Protected);Analytical Chemistry;Biochemistry;Boc-Amino Acids;Enantiomer Excess & Absolute Configuration Determination;Exciton Chirality CD Methodfor (for Monofunctional Compounds);Boc-Amino acid series;Amino Acids & Derivatives
Safty information about Boc-glycine (CAS NO.4530-20-5) is:
Hazard Codes: Xn,Xi
Risk Statements: 22-41-36/37/38-20/21/22
R22:Harmful if swallowed.
R41:Risk of serious damage to the eyes.
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39-39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S39:Wear eye / face protection.
S36:Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
Boc-glycine , its cas register number is 4530-20-5. It also can be called 2-[(2-Methylpropan-2-yl)oxycarbonylamino]acetic acid ; Glycine, N-[(1,1-dimethylethoxy)carbonyl]- ; N-(tert-Butoxycarbonyl)glycine ; Nalpha-tert-Butyloxycarbonylglycine ; t-Butoxycarbonylglycine ; Glycine, N-carboxy-, N-tert-butyl ester (8CI) .It is a white to off-white powder.
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