Hydrochloric Acid → HCID 57264003, compound

HRID 615353Notes

Reaction equation

HRID 615353 reaction equation
[SH:1][C@@H:2]([CH3:13])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]([OH:12])=[O:11])=[O:4].C(=O)([O-])[O-].[K+].[K+].Br[CH:21]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:22]([OH:24])=[O:23].Cl>O>[C:22]([CH:21]([S:1][C@@H:2]([CH3:13])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]([OH:12])=[O:11])=[O:4])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 860202-Bromo-4-phenylbutanoic acidHCID 11171702HCID 11171702, compound

Product 1

HCID 57264003HCID 57264003, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(2S)-1-[(2S)-2-Mercaptopropanoyl]-2-pyrrolidinecarboxylic acid (2.0 g), potassium carbonate (2.8 g) and 2-bromo-4-phenylbutanoic acid (2.9 g) were dissolved in water (40 ml), and stirred overnight at room temperature. The reaction mixture was acidified with 6N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residual oil was purified by silica gel column chromatography to give 2.3 g (62%) of the titled compound: [α]D23 -82.2° (c=1.2, MeOH). IR (KBr, cm-1): 1740, 1720, 1610, 1455, 1438, 1185, 748, 700.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residual oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-813597cfed6d4bbd94846c4f5feb211d
Source dataset
uspto-grants-1985_02
Patent number
US04499102

Reaction notes

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