(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)-propionic acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl ester

HRID 915269Notes

Reaction equation

HRID 915269 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.C(Cl)(=O)OCOC(=O)CC>ClCCl>[O:34]=[S:30]1(=[O:33])[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])[CH2:11][CH3:12])=[O:6])[O:19][C:18]3=[O:20])=[CH:22][C:23]=2[F:35])[CH2:28][CH2:29]1

Participants

4

Reactant 2

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 esterHCID 14800977Propanoyloxymethyl Carbonochloridate

Product 1

HCID 58958565(S)-propionic acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 mg, 1.5 mmol), dichloromethane (14 mL) and propanoyloxymethyl carbonochloridate (7b) gave the titled product in 75% yield (520.9 mg, 1.10 mmol). 1H NMR (400 MHz, CDCl3): δ 7.48 (dd, 1H), 7.24 (t, 1H), 7.16 (dd, 1H), 5.74 (q, 2H), 5.28 (t, 1H), 3.12-3.18 (m, 4.83 (m, 1H), 4.05 (t, 1H), 3.79 (dd, 1H), 3.67 (ddd, 1H), 3.56 (dt, 1H), 3.12-3.18(m, 4H), 3.10 (dt, 1H), 2.32-2.46 (m, 4H), 2.17-2.20 (m, 2H), 1.12 (t, 3H). MS-APCI (m/z+): 473 (M+H).

Sources & evidence

ORD record
ord-3d9718084fae4d6383472490911c21db
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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