Triethylamine → 4-Nitrophenyl [(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methylcarbamate Hydrochloride

HRID 1371393Notes

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:12][N:13]1[CH2:18][CH2:17][O:16][C@@H:15]([CH2:19][NH2:20])[CH2:14]1.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1)=[O:27]>ClCCl>[ClH:8].[Cl:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:12][N:13]1[CH2:18][CH2:17][O:16][C@@H:15]([CH2:19][NH:20][C:26](=[O:27])[O:28][C:29]2[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)[CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of triethylamine (0.101 ml) and Intermediate 11 (2.0 g) in dichloromethane (20 ml) was added dropwise to a solution of 4-nitrophenyl chloroformate (1.62 g) in dichloromethane (10 ml) with stirring at 0° C. under nitrogen. The solution was stirred for 3 h at 0° C., allowed to warm to 20° C., and stand for 18 h. The volatile components were evaporated in vacuo, and the residue was purified by Biotage flash chromatography on silica gel (90 g cartridge), eluting initially with 10% methanol in dichloromethane and subsequently with 20% methanol in dichloromethane, to give the title compound as a light brown solid (2.5 g).

Workup

stirringThe solution was stirred for 3 h at 0° C.
temperatureto warm to 20° C.
customThe volatile components were evaporated in vacuo
customthe residue was purified by Biotage flash chromatography on silica gel (90 g cartridge)
washeluting initially with 10% methanol in dichloromethane and subsequently with 20% methanol in dichloromethane

Sources & evidence

ORD record: ord-40d13304da7a4f6b96b6ea43c50d8c8d
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157457B2

Reaction notes

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