Triethylamine → (S)-(-)-N-[[2-Oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide

HRID 428746Notes

Reaction equation

CC(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25]O)[O:22][C:21]3=[O:27])=[CH:16][C:15]=2[F:28])[CH2:10][CH2:9]1)=O)(C)C.[CH2:29]([N:31](CC)CC)[CH3:30].CS(Cl)(=O)=[O:38]>C(Cl)Cl>[O:27]=[C:21]1[N:20]([C:17]2[CH:18]=[CH:19][C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[C:15]([F:28])[CH:16]=2)[CH2:24][C@H:23]([CH2:25][NH:31][C:29](=[O:38])[CH3:30])[O:22]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (R)-(-)-4-[4-[5-(hydroxymethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (EXAMPLE 20, Step 5, 970 mg) and triethylamine (0.50 mL) in dry methylene chloride (9.5 mL) at 0° C. under N2 is treated with methanesulfonyl chloride (0.20 mL) dropwise. The resulting mixture is stirred at 0° C. for one hour, diluted with methylene chloride (40 mL), washed with water (10 mL), saturated aqueous sodium bicarbonate (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound, mp 163-165° C.

Workup

washwashed with water (10 mL), saturated aqueous sodium bicarbonate (10 mL) and saline (10 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d865a52acdf540418b4015127c9463a7
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313307B1

Reaction notes

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