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

HRID 1746626Notes

Reaction equation

HRID 1746626 reaction equation
C(N(CC)CC)C.CS(C)=O.[C:12]([O:15][C@H:16]1[CH2:20][CH2:19][C@H:18]([CH2:21][OH:22])[C@H:17]1[CH2:23][CH2:24][S:25][C:26]1[S:27][CH:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:30]=1)(=[O:14])[CH3:13].Cl>C(OCC)(=O)C>[C:12]([O:15][C@H:16]1[CH2:20][CH2:19][C@H:18]([CH:21]=[O:22])[C@H:17]1[CH2:23][CH2:24][S:25][C:26]1[S:27][CH:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:30]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 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 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (3.7 mL) and sulfur trioxide•pyridine 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-dbef88a1017f48afa9028958767345c4
Source dataset
uspto-grants-2015_10
Patent number
US09150528B2

Reaction notes

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