Cyclohexanecarbonyl chloride → HCID 18104467, compound

HRID 1765976Notes

Reaction equation

HRID 1765976 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) is dissolved in pyridine 5 mL. Cyclohexanoyl chloride (0.62 mL) is added and the mixture is stirred for 2 hours. The reaction mixture is poured onto hydrochloric acid (1N) and crushed ice. The aqueous mixture is extracted twice with toluene. The combined toluene extracts are concentrated in vacuo to give 1.1 g of crude N-cyclohexanoylphenylalanine methyl ester.

Workup

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

Sources & evidence

ORD record
ord-0190f98ae9d443c49b5a39c3e6e49f77
Source dataset
uspto-grants-2007_06
Patent number
US07229966B2

Reaction notes

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