3-Mercaptopropionic Acid → HCID 15617529, compound

HRID 620561Notes

Reaction equation

HRID 620561 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].O[CH:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=1)[CH2:9][C:10]([O:12]C(C)(C)C)=[O:11]>FC(F)(F)C(O)=O>[C:4]([CH2:3][CH2:2][S:1][CH:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:39])([F:38])[F:40])[CH:32]=1)[CH2:9][C:10]([OH:12])=[O:11])([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 65143-Mercaptopropionic AcidHCID 15617528HCID 15617528, compound

Product 1

HCID 15617529HCID 15617529, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To trifluoroacetic acid (20 ml), cooled to 0° C., was added 3-mercaptopropionic acid (0.26 ml, 3 mmoles) followed by t-butyl 3-hydroxy-3-[2-(7-(3-trifluoromethylphenylthio)heptyl)phenyl]propanoate. The reaction mixture was stirred for 1 hour and evaporated. The resulting residue was diluted with carbon tetrachloride and washed with ice water. The organic layer was dried over sodium sulfate, filtered and evaporated. The resulting oil was flash chromatographed to give the desired product, -log KB value 6.8.

Workup

  1. customevaporated
  2. additionThe resulting residue was diluted with carbon tetrachloride
  3. washwashed with ice water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customchromatographed

Sources & evidence

ORD record
ord-aa7a536e635d409e992dd366ed10c71a
Source dataset
uspto-grants-1989_04
Patent number
US04820719

Reaction notes

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