Acetic Acid → HCID 54374254, compound

HRID 903466Notes

Reaction equation

HRID 903466 reaction equation
FC(F)(F)C(O)=O.C(O)(=O)C.Br[CH:13]([C:31](=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:14]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16].[C:39]([O-:42])(=[S:41])[CH3:40].[Na+]>C(#N)C>[C:39]([S:41][CH:13]([C:31](=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:14]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])(=[O:42])[CH3:40]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 23700354HCID 23700354, compoundHCID 54339840HCID 54339840, compound

Product 1

HCID 54374254HCID 54374254, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 0.01 mole sample of 3-benzoyl-2-(phenyl)propionic acid is dissolved in tetrahydrofuran and 0.01 mole of N,N-carbonyldiimidazole added. After stirring 3 hours at room temperature, 0.01 mole of L-proline t-butyl ester is added. After 24 hours the solvent is removed and 1-[3-benzoyl-2-(phenyl)-propionyl]-L-proline t-butyl ester isolated. The preceding compound is reacted with trifluoroacetic acid to remove the t-butyl group. Separation of isomers A and B is carried out as described for Example 69. Reaction of the isomers with bromine is acetic acid and reaction of the 1-[3-bromo-3-benzoyl-2-(phenyl)propionyl]-L-proline isomers with sodium thioacetate in acetonitrile as for Example 69 gives the products of the example. The product from isomer A is separated by chromatography to give [S-(R*,R*)] and [S-(R*,S*)]-1-[3-acetylthio-3-benzoyl-2-(phenyl)propionyl]-L-proline.

Workup

  1. customto remove the t-butyl group
  2. customSeparation of isomers A and B
  3. customReaction of the isomers with bromine
  4. customgives the products of the example
  5. customThe product from isomer A is separated by chromatography

Sources & evidence

ORD record
ord-c9b6042b332d4b93b9b3a284251cd3c8
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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