Trifluoroacetic acid → 2-amino-3-methylbutyric acid 2-{[6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carbonyl]-aminooxy}-ethylester trifluoroacetic acid salt

HRID 1767864Notes

Reaction equation

HRID 1767864 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:20]([NH:22][O:23][CH2:24][CH2:25][O:26][C:27](=[O:40])[CH:28]([NH:32]C(OC(C)(C)C)=O)[CH:29]([CH3:31])[CH3:30])=[O:21])=[CH:11][C:12]3[N:16]([CH3:17])[CH:15]=[N:14][C:13]=3[C:18]=2[F:19])=[C:4]([Cl:41])[CH:3]=1.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:20]([NH:22][O:23][CH2:24][CH2:25][O:26][C:27](=[O:40])[CH:28]([NH2:32])[CH:29]([CH3:31])[CH3:30])=[O:21])=[CH:11][C:12]3[N:16]([CH3:17])[CH:15]=[N:14][C:13]=3[C:18]=2[F:19])=[C:4]([Cl:41])[CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86592879HCID 86592879, compound

Product 1

HCID 865928802-amino-3-methylbutyric acid 2-{[6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carbonyl]-aminooxy}-ethylester trifluoroacetic acid salt

Procedure

A mixture of 2-tert-butoxycarbonylamino-3-methylbutyric acid 2-{[6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carbonyl]-aminooxy}-ethylester and its N-acylated isomer (0.6 g) were treated with 1.5 mL of trifluoroacetic acid for 0.5 hours. An HPLC trace of the reaction mixture showed the reaction was complete. The mixture was concentrated on a rotary evaporator and pumped on high vacuum to give yellow oil (0.9 g). The deprotected samples were submitted for HPLC purification to give purified product as a trifluoroacetic acid salt.

Workup

  1. concentrationThe mixture was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-a87984851a6d42619ef951191ac4dd9b
Source dataset
uspto-grants-2007_06
Patent number
US07235537B2

Reaction notes

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