Cyclohexanecarbonyl chloride → HCID 18104467, compound

HRID 963923Notes

Reaction equation

HRID 963923 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-7987ff777a344e45b1c089cb00461ea7
Source dataset
uspto-grants-1998_06
Patent number
US05766633

Reaction notes

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