Cyclohexanecarbonyl chloride → HCID 18104467, compound

HRID 990595Notes

Reaction equation

HRID 990595 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].[CH:14]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH:5][C:20]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:21]

Participants

4

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 736234L-Phenylalanine, methyl ester

Product 1

HCID 18104467HCID 18104467, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phenylalanine methyl ester (1 g., 0.0046 moles) was dissolved in pyridine 5 mL. Cyclohexanoyl chloride (0.62 mL) was added and the mixture was stirred for 2 hours. The reaction mixture was poured onto hydrochloric acid (1N) and crushed ice. The aqueous mixture was extracted twice with toluene. The combined toluene extracts were concentrated in vacuo to give 1.1 g of crude N-cyclohexanoylphenylalanine methyl ester.

Workup

  1. additionThe reaction mixture was poured onto hydrochloric acid (1N)
  2. customcrushed ice
  3. extractionThe aqueous mixture was extracted twice with toluene
  4. concentrationThe combined toluene extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-55a547ba90a24700bdc17a6cda5ac964
Source dataset
uspto-grants-2002_10
Patent number
US06461643B2

Reaction notes

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