(S)-4-Benzyl-2-oxazolidinone → HCID 18341341, compound

HRID 2300012Notes

Reaction equation

HRID 2300012 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:21])[CH2:15][C:16]1SC=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:22]1C=CC(CC(Cl)=O)=[CH:23]1.C([C@H]1COC(=O)N1)C1C=CC=CC=1>>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:21])[CH2:15][C:16]1[CH:20]=[CH:19][S:22][CH:23]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 27606223-Thiopheneacetyl chlorideHCID 18341340HCID 18341340, compound

Product 1

HCID 18341341HCID 18341341, compoundYield 68%

Procedure

According to the procedure described in Example 17(a) for the preparation of 4(S)-benzyl-3-(2-thien-2-yl-acetyl)-2-oxazolidinone, 3-thiopheneacetyl chloride and (S)-(−)-4-benzyl-2-oxazolidinone furnished in 68% yield 4(S)-benzyl-3-(2-thien-3-yl-acetyl)-2-oxazolidinone as a solid, mp 80-1° C. 1H NMR: δ 7.33-7.24 (m, 5H), 7.15-7.09 (m, 3H), 4.72-4.65 (m, 1H), 4.39, 4.28 (AB quartet, 2H, J=15.9 Hz), 4.22-4.15 (m, 2H), 3.26 (dd, 1H, J=3.2, 13.4 Hz), 2.77 (dd, 1H, J=9.4, 13.4 Hz). Anal. Calculated for C16H15NO3S: C, 63.77; H, 5.02; N, 4.65; S, 10.64. Found: C, 63.80; H, 5.04; N, 4.69; S, 10.70.

Sources & evidence

ORD record
ord-661b981400c84276b7d6b5ff6dcc6ac7
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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