3-Mercaptopropionic Acid → HCID 15617412, compound

HRID 2082604Notes

Reaction equation

HRID 2082604 reaction equation
[Na].[SH:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=[CH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CO>[C:5]([CH2:4][CH2:3][S:2][CH:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 65143-Mercaptopropionic AcidHCID 5360545SodiumHCID 54421954HCID 54421954, compound

Product 1

HCID 15617412HCID 15617412, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium (155.5 mmoles) was added slowly to methanol (200 ml ) under an atmosphere of argon. The mixture was cooled to 0° C. in an ice bath and 3-mercaptopropionic acid (78 mmoles) was added dropwise. This mixture was stirred for 30 minutes and the compound of Example 9 (a) (7.8 mmoles) was added dropwise. The reaction mixture was stirred for 24 hours. The solvent was evaporated. The residue was taken up in ice water and acidifed with 10% phosphoric acid to a pH of 6.5. The product was extracted into ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and evaporated. The resulting residue was flash chromatographed with 1.0% methanol and 1.0% formic acid in methylene chloride. This provided the product as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 24 hours
  2. customThe solvent was evaporated
  3. extractionThe product was extracted into ethyl acetate
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customchromatographed with 1.0% methanol and 1.0% formic acid in methylene chloride

Sources & evidence

ORD record
ord-9e3d1e6429d242b6b68903f43c8433f8
Source dataset
uspto-grants-1993_02
Patent number
US05189226

Reaction notes

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