Hydrochloric Acid → HCID 57126089, compound

HRID 1034494Notes

Reaction equation

HRID 1034494 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][C@H:9]1[CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]([O-:33])(=[S:32])[CH3:31].[K+].C(OCC)(=O)C.Cl>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([S:32][C:30](=[O:33])[CH3:31])[CH2:10][C@H:9]1[CH2:18][N:19]1[C:20](=[O:29])[C:21]2=[CH:28][CH:27]=[CH:26][CH:25]=[C:22]2[C:23]1=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23670855Potassium ethanethioateHCID 57239737HCID 57239737, compound

Product 1

HCID 57126089HCID 57126089, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2S,4R)-1-t-butoxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidine (3 g) in dimethylformamide (30 ml), potassium thioacetate (1.65 g) is added. The mixture is stirred at 60° C. for 3.5 hours. The reaction mixture is poured into a mixture of ethyl acetate and dilute hydrochloric acid. The organic layer is taken, washed with water, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give (2S,4S)-1-t-butoxycarbonyl-2-phthalimidomethyl-4-acetylthiopyrrolidine (2.12 g). Yield: 74%. Orange colored syrup. NMR δ(CDCl3) ppm: 1.30, 1.39(2×s, 9H), 1.6 to 2.0(m, 1H), 2.34(s, 3H), 2.4 to 2.67(m, 1H), 3.15 to 3.3(m, 1H), 3.65 to 4.55(m, 5H), 7.6 to to 8.0(m, 4H). IR ν (CHCl3) cm-1 : 1774, 1715, 1688.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1dde467375f84b3c8923bce66467af17
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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