L-Proline → HCID 54491809, compound

HRID 903456Notes

Reaction equation

HRID 903456 reaction equation
ClC1C=CC(C(CCC(O)=O)=O)=CC=1C(F)(F)F.N1CCC[C@H]1C(O)=O.[Cl:27][C:28]1[CH:47]=[CH:46][C:31]([C:32]([CH2:34][CH2:35][C:36]([N:38]2[CH2:45][CH2:44][CH2:43][C@H:39]2[C:40]([OH:42])=[O:41])=[O:37])=[O:33])=[CH:30][C:29]=1[C:48]([F:51])([F:50])[F:49].[C:52]([O-:55])(=[S:54])[CH3:53].[K+]>C(O)C.O>[C:52]([S:54][CH:34]([C:32](=[O:33])[C:31]1[CH:46]=[CH:47][C:28]([Cl:27])=[C:29]([C:48]([F:51])([F:49])[F:50])[CH:30]=1)[CH2:35][C:36]([N:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40]([OH:42])=[O:41])=[O:37])(=[O:55])[CH3:53]

Participants

6

Reactant 4

HCID 145742L-ProlineHCID 23337572HCID 23337572, compoundHCID 23670855Potassium ethanethioateHCID 70526367HCID 70526367, compound

Product 1

HCID 54491809HCID 54491809, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

The preceding compound is converted to 3-(4-chloro-3-trifluoromethylbenzoyl)propionic acid, hydroxysuccinimide ester and coupled to L-proline as in Example 16. The 1-([3-(4-chloro-3-trifluoromethylbenzoyl)propionyl]-L-proline is brominated as in Example 20 and the product reacted with potassium thioacetate in ethanol-water (1:1) 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-64b89ead6b534d6dba270a4ad91de205
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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