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

HRID 915273Notes

Reaction equation

HRID 915273 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(OCOC(=O)CC)=O)(=O)C.[C:36](Cl)(=[O:46])[O:37][CH2:38][O:39][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]>ClCCl>[O:34]=[S:30]1(=[O:33])[CH2:29][CH2:28][CH:27]([C:24]2[CH:25]=[CH:26][C:21]([N:17]3[CH2:16][C@H:15]([CH2:14][NH:4][C:36]([O:37][CH2:38][O:39][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42])=[O:46])[O:19][C:18]3=[O:20])=[CH:22][C:23]=2[F:35])[CH2:32][CH2:31]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 148009802,2-Dimethyl-propanoyloxymethyl carbonochloridate

Product 1

HCID 58958556(S)-2,2-dimethyl-propionic acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl esterYield 85%

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) (472.0 mg, 1.38 mmol) in dichloromethane (13 mL) and 2,2-dimethyl-propanoyloxymethyl carbonochloridate (7f) gave the titled product in 85% yield (585.6 mg, 1.17 mmol).

Sources & evidence

ORD record
ord-e34b3deb3c6649aa990e5c5c8aab0e79
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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