Bromine → 1-[3-bromo-3-(3,4-dichlorobenzoyl)propionyl]-L-proline

HRID 903455Notes

Reaction equation

HRID 903455 reaction equation
ClC1C=C(C=CC=1Cl)C(CCC(O)=O)=O.N1CCC[C@H]1C(O)=O.[Cl:24][C:25]1[CH:26]=[C:27]([CH:42]=[CH:43][C:44]=1[Cl:45])[C:28]([CH2:30][CH2:31][C:32]([N:34]1[CH2:41][CH2:40][CH2:39][C@H:35]1[C:36]([OH:38])=[O:37])=[O:33])=[O:29].[Br:46]Br>C(O)(=O)C>[Br:46][CH:30]([C:28](=[O:29])[C:27]1[CH:42]=[CH:43][C:44]([Cl:45])=[C:25]([Cl:24])[CH:26]=1)[CH2:31][C:32]([N:34]1[CH2:41][CH2:40][CH2:39][C@H:35]1[C:36]([OH:38])=[O:37])=[O:33]

Participants

6

Reactant 4

HCID 24408BromineHCID 145742L-ProlineHCID 2897634-(3,4-Dichlorophenyl)-4-oxobutyric acidHCID 537825561-[3-(3,4-dichlorobenzoyl)propionyl]-L-proline

Product 1

HCID 544129371-[3-bromo-3-(3,4-dichlorobenzoyl)propionyl]-L-proline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The preceding compound is heated with 6 N hydrochloric acid to give 3-(3,4-dichlorobenzoyl)propionic acid. As described in Example 15, 3-(3,4-dichlorobenzoyl)propionic acid, hydroxysuccinimide ester is prepared and coupled to L-proline as in Example 16. The 1-[3-(3,4-dichlorobenzoyl)propionyl]-L-proline in acetic acid is reacted with bromine as in Example 20 to give 1-[3-bromo-3-(3,4-dichlorobenzoyl)propionyl]-L-proline.

Workup

  1. customis prepared

Sources & evidence

ORD record
ord-eb42c77cd8a14aacac1ee69226cb38fd
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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