Bromine → 1-[3-bromo-3-(3-trifluoromethylbenzoyl)propionyl]-L-proline

HRID 903454Notes

Reaction equation

HRID 903454 reaction equation
FC(F)(F)C1C=C(C=CC=1)C(CCC(O)=O)=O.N1CCC[C@H]1C(O)=O.[F:26][C:27]([F:49])([F:48])[C:28]1[CH:29]=[C:30]([CH:45]=[CH:46][CH:47]=1)[C:31]([CH2:33][CH2:34][C:35]([N:37]1[CH2:44][CH2:43][CH2:42][C@H:38]1[C:39]([OH:41])=[O:40])=[O:36])=[O:32].[Br:50]Br>C(O)(=O)C>[Br:50][CH:33]([C:31](=[O:32])[C:30]1[CH:45]=[CH:46][CH:47]=[C:28]([C:27]([F:26])([F:48])[F:49])[CH:29]=1)[CH2:34][C:35]([N:37]1[CH2:44][CH2:43][CH2:42][C@H:38]1[C:39]([OH:41])=[O:40])=[O:36]

Participants

6

Reactant 4

HCID 24408BromineHCID 145742L-ProlineHCID 134088364-Oxo-4-(3-trifluoromethylphenyl)butyric acidHCID 536683631-[3-(3-trifluoromethylbenzoyl)propionyl]-L-proline

Product 1

HCID 540986871-[3-bromo-3-(3-trifluoromethylbenzoyl)propionyl]-L-proline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

As described in Example 15, 3-(3-trifluoromethylbenzoyl)propionic acid, hydroxysuccinimide ester is prepared and coupled to L-proline as in Example 16. The 1-[3-(3-trifluoromethylbenzoyl)propionyl]-L-proline in acetic acid is reacted with bromine as in Example 20 to give 1-[3-bromo-3-(3-trifluoromethylbenzoyl)propionyl]-L-proline. The preceding compound is 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. customis prepared

Sources & evidence

ORD record
ord-56d6cc1ee1f34d31aa644ee31479ded1
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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