Dicyclohexylcarbodiimide → (4S)-3-{[(4-Methoxybenzyl)thio]acetyl}-4-phenyl-1,3-oxazolidin-2-one

HRID 254110Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][S:8][CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:30]1([C@H:36]2[CH2:40][O:39][C:38](=[O:41])[NH:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][CH2:9][C:10]([N:37]2[C@@H:36]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:40][O:39][C:38]2=[O:41])=[O:12])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(4-Methoxy-benzylsulfanyl)-acetic acid (1.3 g, 6.1 mmol) was dissolved in dry DCM (40 ml) and cooled to 0° C. N,N′-dicyclohexylcarbodiimide (6.1 g, 6.1 mmol) and DMAP (1.6 g, 12.9 mmol) were added and the mixture was stirred for 30 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (1.0 g, 6.1 mol) was added and the mixture was stirred at room temperature for 24 hours. The mixture was filtrated, concentrated under reduced pressure and purified by flash-chromatography (Hex:EtOAc 8:2 then 1:1). This afforded 1.7 g (77%) of the title compound as a white solid. NMR (200 MHz): 3.46-3.59 (m, 3H), 3.74-3.76 (m, 4H), 4.23-4.28 (m, 1H), 4.68 (t, 1H), 5.38-5-42 (m, 1H), 6.78 (d, 2H), 7.14 (d, 2H), 7.32-7.40 (m, 5H).

Workup

stirringthe mixture was stirred at room temperature for 24 hours
filtrationThe mixture was filtrated
concentrationconcentrated under reduced pressure
custompurified by flash-chromatography (Hex

Sources & evidence

ORD record: ord-726368edfa0a4eefa79875aba894a438
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07871998B2

Reaction notes

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