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

HRID 915274Notes

Reaction equation

HRID 915274 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:47])[O:37][CH2:38][O:39][C:40](=[O:46])[CH2:41][C:42]([CH3:45])([CH3:44])[CH3:43]>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:46])[CH2:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:47])[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 588261543,3-Dimethyl-butyroxymethyl carbonochloridate

Product 1

HCID 58958566(S)-3,3-dimethyl-butyric acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl esterYield 46%

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) (589.0 mg, 1.72 mmol) in dichloromethane (14 mL) and 3,3-dimethyl-butyroxymethyl carbonochloridate (7 g) gave the titled product in 46% yield (407.2 mg, 0.79 mmol). 1H NMR (400 MHz, CDCl3): δ 7.48 (dd, 1H), 7.24 (t, 1H), 7.16 (dd, 1H), 5.73 (q, 2H), 5.26 (t, 1H), 4.75-4.82 (m, 1H), 4.05 (t, 1H), 3.78 (dd, 1H), 3.68 (ddd, 1H), 3.56 (dt, 1H), 3.13-3.19 (m, 4H), 3.10 (dt, 1H), 2.35-2.46 (m, 2H), 2.16-2.25(m, 4H), 1.00 (s, 9H).

Sources & evidence

ORD record
ord-abfeb28618824e66b2300abee12d1055
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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