Hydrochloric Acid → HCID 57754840, compound

HRID 2387587Notes

Reaction equation

HRID 2387587 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][C:11]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]3=[O:34])=[CH:20][C:19]=2[F:35])([OH:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO>[F:35][C:19]1[CH:20]=[C:21]([N:24]2[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]2=[O:34])[CH:22]=[CH:23][C:18]=1[O:17][CH2:16][C:11]1([OH:15])[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67278833HCID 67278833, compound

Product 1

HCID 57754840HCID 57754840, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 334 mg 4-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-hydroxy-azepane-1-carboxylic acid tert-butyl ester (MW: 495.55, 0.674 mmol) in 3 ml of a 1.25 M anhydrous hydrogen chloride solution in methanol was stirred at 35° C. for four hours. The solvent was evaporated under reduced pressure. The residue was dissolved in 4 ml water and the water layer neutralized to pH 7 with a saturated sodium bicarbonate solution. The water was evaporated and the residue dissolved in 30 ml of a 9/1 dichloromethane/methanol mixture. The unsoluble salt were filtered and the filtrate evaporated to dryness to afford off white solid. Yield 266 mg, quant. MS: 395.8 (M+H)+, 440.6 (M+HCOO−), Method ESI+, ESI−.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in 4 ml water
  3. customThe water was evaporated
  4. dissolutionthe residue dissolved in 30 ml of a 9/1 dichloromethane/methanol mixture
  5. filtrationThe unsoluble salt were filtered
  6. customthe filtrate evaporated to dryness
  7. customto afford off white solid

Sources & evidence

ORD record
ord-92f19e78cc7942468f486db3bf693225
Source dataset
uspto-grants-2012_09
Patent number
US08268812B2

Reaction notes

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