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

HRID 254094Notes

Reaction equation

HRID 254094 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:7][O:6][C:5]([CH2:15][S:16][CH2:17][C:18](O)=[O:19])([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[O:4][CH2:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[C:37]1([C@H:43]2[CH2:47][O:46][C:45](=[O:48])[NH:44]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:21])[CH2:7][O:6][C:5]([CH2:15][S:16][CH2:17][C:18]([N:44]2[C@@H:43]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:47][O:46][C:45]2=[O:48])=[O:19])([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[O:4][CH2:3]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7304242-Oxazolidinone, 4-phenyl-, (4S)-HCID 66842795({[5,5-Dimethyl-2-(4-methylphenyl)-1,3-dioxan-2-yl]methyl}thio)acetic acid

Product 1

HCID 66843224(4S)-3-[({[5,5-Dimethyl-2-(4-methylphenyl)-1,3-dioxan-2-yl]methyl}thio)acetyl]-4-phenyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

({[5,5-Dimethyl-2-(4-methylphenyl)-1,3-dioxan-2-yl]methyl}thio)acetic acid (8.7 g, 28.0 mmol) was dissolved in dry CH2Cl2 (120 ml) and cooled to 0° C. N,N′-Dicyclohexylcarbodiimide (DCC, 6.35 g, 30.8 mmol) in 30 ml of CH2Cl2 and 4-(dimethylamino)pyridine (DMAP, 6.85 g, 56.1 mmol) were added. The mixture was stirred at 0° C. for 30 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (4.57 g, 28.0 mmol) was added and the mixture was stirred at room temperature for 19 h. The mixture was filtered, concentrated under reduced pressure and purified by flash-chromatography (hexane:EtOAc 5:1 then 4:1). This afforded 7.07 g (55%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.2 (s, 3H), 2.4 (s, 3H), 2.8 (s, 2H), 3.4 (s, 4H), 3.8 (s, 2H), 4.3 (dd, 1H), 4.7 (t, 1H), 5.4 (dd, 1H), 7.2-7.5 (m, 9H).

Workup

  1. stirringthe mixture was stirred at room temperature for 19 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash-chromatography (hexane:EtOAc 5:1

Sources & evidence

ORD record
ord-8cd738f36f99466e86514728e0b28f8d
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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