Hydrochloric Acid → Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-formylcyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate

HRID 1960056Notes

Reaction equation

HRID 1960056 reaction equation
C(N(CC)CC)C.[S].[C:9]([O:12][C@H:13]1[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[C@H:14]1[CH2:20][CH2:21][S:22][C:23]1[S:24][CH:25]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=1)(=[O:11])[CH3:10].Cl>C(OCC)(=O)C.CS(C)=O>[C:9]([O:12][C@H:13]1[CH2:17][CH2:16][C@H:15]([CH:18]=[O:19])[C@H:14]1[CH2:20][CH2:21][S:22][C:23]1[S:24][CH:25]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=1)(=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 5362487SulfurHCID 15979344Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-(hydroxymethyl)cyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate

Product 1

HCID 86634273Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-formylcyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylateYield 99.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (3.7 mL) and sulfur trioxidepyridine complex (1.7 g) were added to a dimethyl sulfoxide (4.0 mL)/ethyl acetate (8.0 mL) solution of ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-(hydroxymethyl)cyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate (500 mg) (see compound 7 described in the pamphlet of International Publication No. WO 2006/129788) at 10° C., followed by stirring at room temperature for 30 min. To the reaction solution, 1 N hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine; dried with anhydrous sodium sulfate; and concentrated to obtain the title compound (497 mg) having the following physical properties:

Workup

  1. customat 10° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationand concentrated

Sources & evidence

ORD record
ord-4f42aaeb6e73450299016bb719c1eb41
Source dataset
uspto-grants-2013_04
Patent number
US08410281B2

Reaction notes

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