Dicyclohexylcarbodiimide → (4S)-3-[({[2-(1,3-Benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetyl]-4-phenyl-1,3-oxazolidin-2-one

HRID 603916Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:18][S:19][CH2:20][C:21](O)=[O:22])[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[CH2:12][O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C1(N=C=NC2CCCCC2)CCCCC1.[C:39]1([C@H:45]2[CH2:49][O:48][C:47](=[O:50])[NH:46]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:18][S:19][CH2:20][C:21]([N:46]4[C@@H:45]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[CH2:49][O:48][C:47]4=[O:50])=[O:22])[O:11][CH2:12][C:13]([CH3:16])([CH3:17])[CH2:14][O:15]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

({[2-(1,3-Benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid (Method 13) (12.7 g, 37.4 mmol) was dissolved in dry CH2Cl2 (150 ml) and given 0° C. N,N′-Dicyclohexylcarbodiimide (DCC, 8.48 g, 37.4 mmol) and 4-(dimethylamino)pyridine (DMAP, 9.13 g, 74.8 mmol) were added and the mixture was stirred at 0° C. for 20 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (6.10 g, 37.4 mmol) was added and the mixture was stirred at room temperature for 16 hours. The mixture was filtrated, concentrated under reduced pressure and purified by flash-chromatography (heptane:EtOAc 2:1). This afforded the title compound.

Workup

customgiven 0° C
stirringthe mixture was stirred at room temperature for 16 hours
filtrationThe mixture was filtrated
concentrationconcentrated under reduced pressure
custompurified by flash-chromatography (heptane:EtOAc 2:1)

Sources & evidence

ORD record: ord-0979e722f2b94626874193b25d02c1e2
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906502B2

Reaction notes

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