Conditions | Yield |
---|---|
In water at 40 - 50℃; for 3h; | 70% |
With acetic acid | |
In dichloromethane |
(2S,4R)-N-acetyl-4-benzoyloxy-proline
oxaceprol
Conditions | Yield |
---|---|
With sodium hydroxide |
4R-4-hydroxyproline
oxaceprol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH / 0 °C / anschliessend Behandeln mit Benzoylchlorid 2: aqueous NaOH View Scheme |
Conditions | Yield |
---|---|
With acetyl chloride Reflux; | 99% |
oxaceprol
(1S,4S)-5-acetyl-2-oxa-5-azabicyclo<2.2.1>heptan-3-one
Conditions | Yield |
---|---|
90% | |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Ambient temperature; | 70% |
tert-butyldimethylsilyl chloride
oxaceprol
(4R)-1-Acetyl-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-L-proline
Conditions | Yield |
---|---|
Stage #1: tert-butyldimethylsilyl chloride; oxaceprol With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; Stage #2: With sodium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 1.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; methanol; water pH=3; | 84% |
Stage #1: tert-butyldimethylsilyl chloride; oxaceprol With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 10℃; for 1h; Stage #2: With water In acetonitrile for 0.416667h; |
oxaceprol
(1R,4R)-5-acetyl-2-oxa-5-azabicyclo[2.2.1]heptan-3-one
Conditions | Yield |
---|---|
With acetic anhydride at 90℃; for 7h; | 82% |
With acetic anhydride at 20 - 90℃; for 71h; Inert atmosphere; | 45% |
Conditions | Yield |
---|---|
With pyridine for 2h; Ambient temperature; | 75% |
methanol
oxaceprol
methyl (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere; | 66% |
With thionyl chloride at 0℃; Reflux; | 29% |
benzylamine
oxaceprol
Conditions | Yield |
---|---|
With tris(2,2,2-trifluoroethyl) borate at 100℃; under 760.051 Torr; for 5h; | 50% |
1,3-dimethyl-6-methoxy-9H-pyrimido<4,5-b>indole-2,4-dione
oxaceprol
methyl (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylate
Conditions | Yield |
---|---|
With hydrogenchloride for 23h; Heating; | 40% |
1,3-thiazolidine
oxaceprol
Conditions | Yield |
---|---|
Stage #1: 1,3-thiazolidine; oxaceprol With 4-methyl-morpholine; benzotriazol-1-ol In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 25 - 30℃; for 24h; | 33% |
1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine
oxaceprol
(2S,4R)-1-acetyl-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
Conditions | Yield |
---|---|
Stage #1: oxaceprol With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h; Inert atmosphere; Stage #2: 1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; Inert atmosphere; | 32% |
oxaceprol
N-[(3S,4R)-1-((2S,4R)-1-acetyl-4-hydroxy-pyrrolidine-2-carbonyl)-4-phenyl-pyrrolidin-3-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20 - 40℃; for 48h; | 29% |
diazomethane
oxaceprol
methyl (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylate
Conditions | Yield |
---|---|
With 1,4-dioxane; diethyl ether |
oxaceprol
methyl iodide
(2S,4R)-N-acetyl-4-methoxyproline methyl ester
Conditions | Yield |
---|---|
With acetone; silver(l) oxide |
oxaceprol
(4R)-N-Acetyl-2-methoxypyrrolidin-4-ol
Conditions | Yield |
---|---|
With triethylamine In methanol at 15℃; electrolyse; galvanostatic conditions, anode - Pt (disk), cathode - Pt (wire), i=260 mA/cm2 (2.5 F/mol); Yield given; |
N-<4-amino-5-(1,3-benzothiazol-2-yl)-5-hydroxypentyl>-N'-<(4-methoxy-2,3,6-trimethylphenyl)sulfonyl>guanidine
oxaceprol
C30H40N6O7S2
Conditions | Yield |
---|---|
With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; |
oxaceprol
cis-hydroxy-D-proline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 82 percent / Ac2O / 7 h / 90 °C 2: 75 percent / aq. HCl / 2 h / Heating View Scheme |
oxaceprol
(2R,4R)-N-acetyl-4-hydroxyproline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 82 percent / Ac2O / 7 h / 90 °C 2: Dowex 50x8 resin / H2O; acetone / 48 h / 20 °C View Scheme |
oxaceprol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / pyridine / 2 h / Ambient temperature 2: 1.) Ac2O / 1.) toluene, 80 deg C, 1 h, 2.) toluene, 80 deg C, 24 h View Scheme |
oxaceprol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / pyridine / 2 h / Ambient temperature 2: 1.) Ac2O / 1.) toluene, 80 deg C, 1 h, 2.) toluene, 80 deg C, 24 h View Scheme |
oxaceprol
(2S,4S)-1-acetyl-4-hydroxyproline methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent 2: Amberlyst 15 / 16 h View Scheme |
oxaceprol
(R)-N-Acetyl-4-hydroxy-2-pyrrolidone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / methanol / 15 °C / electrolyse; galvanostatic conditions, anode - Pt (disk), cathode - Pt (wire), i=260 mA/cm2 (2.5 F/mol) 2: 78 percent / peracetic acid, Amberlyst 15 / CH2Cl2; acetic acid / 216 h / Ambient temperature View Scheme |
oxaceprol
hydroxy L-proline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: dioxane; diethyl ether 2: pyridine 3: aqueous methanol. NaOH / 0 °C 4: aqueous NaOH 5: aqueous HCl View Scheme |
oxaceprol
N-acetyl-cis-4-hydroxy-L-proline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dioxane; diethyl ether 2: pyridine 3: aqueous methanol. NaOH / 0 °C 4: aqueous NaOH View Scheme |
oxaceprol
N-acetyl-trans-4-(tosyloxy)-L-proline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dioxane; diethyl ether 2: pyridine 3: aqueous methanol. NaOH / 0 °C View Scheme |
oxaceprol
(3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dioxane; diethyl ether 2: pyridine View Scheme |
1. Introduction of N-Acetyl-L-hydroxyproline
N-Acetyl-L-hydroxyproline, with the IUPAC name of (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylic acid, is one kind of powder. The product's categories are Pyrrole; API Intermediates; Amino Acids; Hydroxyproline [Hyp]; Peptide Synthesis; Proline Derivatives; Unnatural Amino Acid Derivatives. It is white crystalline powder which is soluble in water. And AC-HYP-OH is an anti-inflammatory drug used in the treatment of osteoarthritis. Additionally, it should be sealed in the container and stored at the normal temperature.
2. Properties of N-Acetyl-L-hydroxyproline
The other characteristics of AC-HYP-OH can be summarized as: (1)ACD/LogP: -2.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.33; (4)ACD/LogD (pH 7.4): -5.66; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.56; (13)Molar Refractivity: 38.91 cm3; (14)Molar Volume: 120.2 cm3; (15)Polarizability: 15.42×10-24 cm3; (16)Surface Tension: 69.6 dyne/cm; (17)Enthalpy of Vaporization: 80.74 kJ/mol; (18)Vapour Pressure: 1.13E-09 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 173.068808; (21)MonoIsotopic Mass: 173.068808; (22)Topological Polar Surface Area: 77.8; (23)Heavy Atom Count: 12; (24)Complexity: 216.
3. Structure Descriptors of N-Acetyl-L-hydroxyproline
You could convert the following datas into the molecular structure:
1. SMILES:O=C(N1[C@H](C(=O)O)C[C@@H](O)C1)C
2. InChI:InChI=1/C7H11NO4/c1-4(9)8-3-5(10)2-6(8)7(11)12/h5-6,10H,2-3H2,1H3,(H,11,12)/t5-,6+/m1/s1
3. InChIKey:BAPRUDZDYCKSOQ-RITPCOANBI
4. Safety Information of N-Acetyl-L-hydroxyproline
Hazard Codes: Xi
Risk Statements: 41
Safety Statements: 26-36
WGK Germany: 3
F: 10
When you are using this chemical, please be cautious about it as the following:
It may cause serious damage to the eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
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