(R)-propionic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester → (S)-benzoic acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl ester

HRID 915276Notes

Reaction equation

HRID 915276 reaction equation
C([N:4]([CH2:14][C@@H:15]1[O:19][C:18](=[O:20])[N:17]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]3[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]3)=[C:23]([F:35])[CH:22]=2)[CH2:16]1)[C:5]([O:7][CH2:8][O:9][C:10](=[O:13])[CH2:11][CH3:12])=[O:6])(=O)C>ClCCl.C(Cl)(=O)OCOC(=O)C1C=CC=CC=1>[O:33]=[S:30]1(=[O:34])[CH2:31][CH2:32][CH:27]([C:24]2[CH:25]=[CH:26][C:21]([N:17]3[CH2:16][C@H:15]([CH2:14][NH:4][C:5]([O:7][CH2:8][O:9][C:10](=[O:13])[C:11]4[CH:12]=[CH:23][CH:22]=[CH:21][CH:26]=4)=[O:6])[O:19][C:18]3=[O:20])=[CH:22][C:23]=2[F:35])[CH2:28][CH2:29]1

Participants

4

Reactant 1

HCID 11386734(R)-propionic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester

Product 1

HCID 58958557(S)-benzoic acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14800986Benzoyloxymethyl chloroformateSolvent

Procedure

Following general procedure C, (S)-5-aminomethyl-3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-oxazolidin-2-one (2) (500.0 mg, 1.5 mmol) in dichloromethane (14 mL) and benzoyloxymethyl carbonochloridate (7k) gave the titled product in 98% yield (744.5 mg, 1.43 mmol). 1H NMR (400 MHz, CDCl3): δ 8.05 (d, 2H), 7.60 (t, 1H), 7.46 (q, 3H), 7.20 (t, 1H), 7.13 (dd, 1H), 5.98 (q, 2H), 5.36 (t, 1H), 4.77-4.83 (m, 1H), 4.05 (t, 1H), 3.80 (dd, 1H), 3.68 (ddd, 1H), 3.57 (dt, 1H), 3.12-3.19 (m, 4H), 3.08 (dt, 1H), 2.31-2.45 (m, 2H), 2.13-2.21 (m, 2H).

Sources & evidence

ORD record
ord-d7bddb933b8f4d67b23fed9a20efe6d1
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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