4-Chlorobenzyl alcohol → HCID 67151716, compound

HRID 1805239Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[Cl:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][OH:41])=[CH:38][CH:37]=1>ClCCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:41][CH2:40][C:39]3[CH:42]=[CH:43][C:36]([Cl:35])=[CH:37][CH:38]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred suspension of (S)-4-[2-(4-isocyanato-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (240 mg) in 1,2-dichloroethane (2 ml) in a pressure tube were added sequentially N,N-diisopropylethylamine (0.24 ml) and 4-chloro-benzyl alcohol (148 mg). The tube was capped and stirring was continued while the reaction mixture was heated at 110° C. for 18 h. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S)-4-{2-[4-(4-chloro-benzyloxycarbonylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (174 mg, 51%) as a colourless amorphous solid. MS (ISP): 508.2 ([{37Cl}M+NH4]+), 506.2 ([{35Cl}M+NH4]+), 491.2 ([{37Cl}M+H]+), 489.2 ([{35Cl}M+H]+), 435.2 ([{37Cl}M+H—C4H8]+), 433.2 ([{35Cl}M+H—C4H8]+).

Workup

customThe tube was capped
temperatureThe mixture was then cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

Sources & evidence

ORD record: ord-68d8ed27b1124fafbb0415cc5df4ad83
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354441B2

Reaction notes

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