Cyclopentanol → N-benzyloxycarbonyl-L-isoleucine cyclopentyl ester

HRID 1006402Notes

Reaction equation

HRID 1006402 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[CH:32]1(O)[CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[CH:32]1([O:18][C:17](=[O:19])[C@H:12]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724772N-[(Phenylmethoxy)carbonyl]-L-isoleucine

Product 1

HCID 54144852N-benzyloxycarbonyl-L-isoleucine cyclopentyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-benzyloxycarbonyl-L-isoleucine (10.0 g, 37.7 mmol) in DCM (150 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (7.94 g, 41.5 mmol), cyclopentanol (3.90 g, 45.2 mmol) and N,N-dimethylaminopyridine (20 mg). The reaction was allowed to stand at room temperature for 18 hours. The reaction mixture was washed with 1M hydrochloric acid, saturated sodium bicarbonate, and brine before drying over magnesium sulphate, filtration and removal of solvent under reduced pressure to leave N-benzyloxycarbonyl-L-isoleucine cyclopentyl ester as a colourless ester as a colourless oil (10.99 g, 87%). 1H-NMR; δ (CDCl3) 7.44-7.30 (5H, m), 5.37-5.34 (1H, m), 5.22-5.18 (1H, m), 5.11 (2H, s), 4.33-4.27 (1H, m), 1.90-1.55 (10H, m), 1.51-1.35 (1H, m), 1.28-1.20 (2H, m), 0.93 (3H, d, J 6.9 Hz) and 0.91 (3H, d, J=7.0 Hz).

Workup

  1. washThe reaction mixture was washed with 1M hydrochloric acid, saturated sodium bicarbonate, and brine
  2. dry with materialbefore drying over magnesium sulphate, filtration and removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-72935978c427442e995dbead91c0710f
Source dataset
uspto-grants-2004_09
Patent number
US06790834B1

Reaction notes

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