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

HRID 254100Notes

Reaction equation

HRID 254100 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:16][S:17][CH2:18][C:19]([OH:21])=O)[O:13][CH2:12][C:11]([CH3:15])([CH3:14])[CH2:10][O:9]2)=[CH:4][CH: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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:16][S:17][CH2:18][C:19]([N:44]3[C@@H:43]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH2:47][O:46][C:45]3=[O:48])=[O:21])[O:9][CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][O:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7304242-Oxazolidinone, 4-phenyl-, (4S)-HCID 66843234({[2-(4-Chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid

Product 1

HCID 66843329(4S)-3-[({[2-(4-Chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetyl]-4-phenyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

({[2-(4-Chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid (2.00 g, 6.05 mmol) was dissolved in dry CH2Cl2 (45 ml) and cooled to 0° C. N,N′-Dicyclohexylcarbodiimide (DCC, 1.43 g, 6.93 mmol) and 4-(dimethylamino)pyridine (DMAP, 1.70 g, 10.4 mmol) were added and the mixture was stirred at 0° C. for 20 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (1.40 g, 11.5 mmol) was added and the mixture was stirred at room temperature for 70 h. The mixture was filtered, concentrated under reduced pressure and purified by flash-chromatography (20%-30% EtOAc in hexane). This afforded 1.27 g (44%) of the title compound as a white solid. 1H-NMR (CDCl3, 300 MHz): δ 0.62 (s, 3H), 1.34 (s, 3H), 2.78 (s, 2H), 3.42 (s, 4H), 3.85 (s, 2H), 4.27-4.33 (dd, 1H), 4.69-4.78 (t, 1H), 5.34-5.42 (dd, 1H), 7.29-7.38 (m, 9H).

Workup

  1. stirringthe mixture was stirred at room temperature for 70 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash-chromatography (20%-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-11d57f68fdf34a5281be35d4ced45ba2
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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