Hydrochloric Acid → 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]-1,3-thiazole-4-carboxylic acid

HRID 1888298Notes

Reaction equation

HRID 1888298 reaction equation
[OH:1][C@@H:2]([C:24]([CH3:30])([CH3:29])[CH2:25][CH2:26][CH2:27][CH3:28])/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][O:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][S:13][C:14]1[S:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[N:18]=1.[OH-].[Na+].Cl>CO>[OH:1][C@@H:2]([C:24]([CH3:29])([CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][O:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][S:13][C:14]1[S:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[N:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66857441ethyl 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

Product 1

HCID 595548242-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]-1,3-thiazole-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound 7 (84.0 mg) in methanol (1.00 mL) was added an aqueous solution of 2N sodium hydroxide (0.19 mL) at 0° C. and the solution was stirred at room temperature for 1 hour. To the reaction solution was added an aqueous solution of 2N hydrochloric acid (0.30 mL). The solution was extracted with ethyl acetate and washed with water and brine. The reaction solution was dried over anhydrous sodium sulfate and concentrated to give the title compound (78.8 mg) having the following physical data.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialThe reaction solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b16b1308d8a642e4900da7eb11e458c4
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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