Hydrochloric Acid → (2R)-3-cyclopentyl-2-(hydroxymethyl)-N-[(phenylmethyl)oxy]propanamide

HRID 1366371Notes

Reaction equation

[CH:1]1([CH2:6][C@H:7]([CH2:11][OH:12])[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH2:14]([O:21][NH2:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.ClCCl>[CH:1]1([CH2:6][C@H:7]([CH2:11][OH:12])[C:8]([NH:22][O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of (2R)-3-cyclopentyl-2-(hydroxymethyl)propanoic acid (18.3 g, 106 mmol), O-benzyl hydroxyamine hydrochloride (18.62 g, 117 mmol) and 4-(dimethylamino)pyridine (28.5 g, 233 mmol) in dichloromethane (110 mL) at 0° C. was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (22.3 g, 117 mmol). The mixture was maintained at 0° C. for 3 h. After this time, 500 mL of 1N cold, aqueous HCl solution was added, and the mixture was stirred for another 30 min. The resulting white solid precipitate was collected by filtration. The precipitate was washed with 1N HCl, with water, and with cold DCM. Drying overnight in a vacuum dessicator provided (2R)-3-cyclopentyl-2-(hydroxymethyl)-N-[(phenylmethyl)oxy]propanamide (19.1 g, 65%). LCMS: (M+H)+: 278.1.

Workup

filtrationThe resulting white solid precipitate was collected by filtration
washThe precipitate was washed with 1N HCl, with water
customDrying overnight in a vacuum dessicator

Sources & evidence

ORD record: ord-28ccd96d9b554866a3cfbfd46029449c
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

Loading…