Cyclopentanol → HCID 54144852, compound

HRID 564688

Reaction equation

HRID 564688 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 54144852HCID 54144852, compoundYield 87.4%

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 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 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, 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. washwas 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-2cdf2262962141ddb9beff53b3b02125
Source dataset
uspto-grants-2001_01
Patent number
US06169075A

Linked notes

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