(+/-)-cis-3-(Carbobenzoxyamino)cyclohexanecarboxylic Acid

Base Information

• Chemical Name: (+/-)-cis-3-(Carbobenzoxyamino)cyclohexanecarboxylic Acid
• CAS No.: 952616-39-6
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 952616-39-6.mol

Synonyms:(+/-)-cis-3-(Carbobenzoxyamino)cyclohexanecarboxylic Acid;(+/-)-cis-3-(Cbz-amino)cyclohexanecarboxylic Acid;)-cis-3-(Carbobenzoxyamino)cyclohexanecarboxylic Acid

Chemical Property of (+/-)-cis-3-(Carbobenzoxyamino)cyclohexanecarboxylic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 113-114 °C
• Boiling Point: 484.653°C at 760 mmHg
• PKA: 4.61±0.10(Predicted)
• Flash Point: 246.91°C
• PSA: 79.12000
• Density: 1.229g/cm³
• LogP: 2.76060
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

(+/-)-cis-3-(Carbobenzoxyamino)cyclohexanecarboxylic Acid >95.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+/-)-cis-3-(Carbobenzoxyamino)cyclohexanecarboxylic Acid

There total 27 articles about (+/-)-cis-3-(Carbobenzoxyamino)cyclohexanecarboxylic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

(+/-)-cis-(3-cyanocyclohexyl)carbamic acid benzyl ester → (+/-)-cis-3-benzyloxycarbonylamino-cyclohexane carboxylic acid (952616-39-6)

Guidance literature:

With nitrilase NIT-107; In phosphate buffer; dimethyl sulfoxide; at 29 - 31 ℃; for 18h; pH=8.00;

DOI:10.1021/jo070776j

Reference yield: 33.0%

3-aminocyclohexanecarboxylic acid (16636-51-4,25912-50-9,34583-99-8,38541-66-1,57043-02-4,81131-39-7,81131-40-0,41235-88-5,933445-51-3,933445-54-6) + benzyl chloroformate (501-53-1,94274-21-2) → (1S,3R)-3-(((benzyloxy)carbonyl)amino)cyclohexanecarboxylic acid (952616-39-6)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 18h;

DOI:10.1021/ml2002423

Reference yield:

3-hydroxycyclohexanecarbonitrile (24056-33-5) → (+/-)-cis-3-benzyloxycarbonylamino-cyclohexane carboxylic acid (952616-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: NaN₃ / dimethylformamide / 60 °C

3: H₂ / Pd/C / methanol / 20 °C / 750.08 Torr

4: K₂CO₃ / ethanol; H₂O / 0 - 20 °C

5: 93 percent / nitrilase NIT-107 / aq. phosphate buffer; dimethylsulfoxide / 18 h / 29 - 31 °C / pH 8.00

With sodium azide; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In methanol; phosphate buffer; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo070776j

upstream raw materials:

3-hydroxycyclohexanecarbonitrile

cyclohexenone

3-oxocyclopentane-1-carbonitrile

(RS)-3-oxocyclohexanecarbonitrile

Downstream raw materials:

N-[(1R,3S)-3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]-pyridin-3-yl)pyrimidin-4-yl]amino]cyclohexyl]morpholine-4-carboxamide

tert-butyl N-[(1R,3S)-3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]cyclohexyl]carbamate

N-[(1R,3S)-3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]cyclohexyl]morpholine-4-carboxamide

(1S,3R)-N₁-[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]cyclohexane-1,3-diamine