3-(3-Fluoro-4-methoxybenzoyl)propionic acid → 1-[3-Acetylthio-3-(3-fluoro-4-methoxybenzoyl)propionyl]-L-proline

HRID 903457Notes

Reaction equation

HRID 903457 reaction equation
FC1C=C(C=CC=1OC)C(CCC(O)=O)=O.N1CCC[C@H]1C(O)=O.[F:25][C:26]1[CH:27]=[C:28]([CH:43]=[CH:44][C:45]=1[O:46][CH3:47])[C:29]([CH2:31][CH2:32][C:33]([N:35]1[CH2:42][CH2:41][CH2:40][C@H:36]1[C:37]([OH:39])=[O:38])=[O:34])=[O:30].[C:48]([O-:51])(=[S:50])[CH3:49].[K+]>C(O)C.O>[C:48]([S:50][CH:31]([C:29](=[O:30])[C:28]1[CH:43]=[CH:44][C:45]([O:46][CH3:47])=[C:26]([F:25])[CH:27]=1)[CH2:32][C:33]([N:35]1[CH2:42][CH2:41][CH2:40][C@H:36]1[C:37]([OH:39])=[O:38])=[O:34])(=[O:51])[CH3:49]

Participants

6

Reactant 4

HCID 676713-(3-Fluoro-4-methoxybenzoyl)propionic acidHCID 145742L-ProlineHCID 23670855Potassium ethanethioateHCID 537100931-[3-(3-fluoro-4-methoxybenzoyl)propionyl]-L-proline

Product 1

HCID 540106161-[3-Acetylthio-3-(3-fluoro-4-methoxybenzoyl)propionyl]-L-proline

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

As described in Example 15, the preceding compound is converted to 3-(3-fluoro-4-methoxybenzoyl)propionic acid, hydroxysuccinimide ester and coupled to L-proline as in Example 16. The 1-[3-(3-fluoro-4-methoxybenzoyl)propionyl]-L-proline m.p. 180°-182° C. is brominated as in Example 20 and the product reacted with potassium thioacetate in ethanol-water as in Example 21 to give the product of the Example as a glass.

Workup

  1. customto give the product of the Example as a glass

Sources & evidence

ORD record
ord-e458afe9c42a43858523aac5a6e5d923
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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