Ammonium Chloride → (R)-4-(3-Hydroxy-1-oxopropyl)-3-[[(S)-1-(phenylmethyloxycarbonyl)-2-pyrrolidinyl]carbonyl]thiazolidine

HRID 1735420Notes

Reaction equation

HRID 1735420 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]([C@@H:13]1[CH2:17][S:16][CH2:15][N:14]1[C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:19])=[O:12])(C(C)(C)C)(C)C.[Cl-].[NH4+]>C(O)(=O)C.C1COCC1.O>[OH:8][CH2:9][CH2:10][C:11]([C@@H:13]1[CH2:17][S:16][CH2:15][N:14]1[C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:19])=[O:12]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 53648898HCID 53648898, compound

Product 1

HCID 54040089(R)-4-(3-Hydroxy-1-oxopropyl)-3-[[(S)-1-(phenylmethyloxycarbonyl)-2-pyrrolidinyl]carbonyl]thiazolidineYield 58.3%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

(R)-4-[3-(tert-Butyldimethylsilyloxy)-1-oxopropyl]-3-[[(S)-1-(phenylmethyloxycarbonyl)-2-pyrrolidinyl]carbonyl]thiazolidine (215 mg) was dissolved in a mixture of acetic acid-THF-water (3:1:1, 3 ml), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into saturated ammonium chloride and extracted with chloroform. The organic layer was washed with water, saturated sodium hydrogencarbonate and saturated brine in order, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative thin-layer chromatography (silica gel, developing solvent: chloroform-methanol) to give the title compound (97 mg) (see Table 5).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water, saturated sodium hydrogencarbonate and saturated brine in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative thin-layer chromatography (silica gel, developing solvent: chloroform-methanol)

Sources & evidence

ORD record
ord-1318387a772849769a62e5985b27846b
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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