Trifluoroacetic acid methylene chloride → Trifluoroacetic acid

HRID 29491Notes

Reaction equation

C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:17]2[C:18]([CH3:47])=[C:19]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([S:36]([NH:39][C@@H:40]([CH:44]([CH3:46])[CH3:45])[C:41]([OH:43])=[O:42])(=[O:38])=[O:37])=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)=[O:22])[O:20][C:16]=2[CH:15]=[CH:14][CH:13]=1)=O)(C)(C)C.[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49].C(Cl)Cl>>[NH2:8][CH2:9][CH2:10][O:11][C:12]1[C:17]2[C:18]([CH3:47])=[C:19]([C:21]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:30]4[CH:35]=[CH:34][C:33]([S:36]([NH:39][C@@H:40]([CH:44]([CH3:45])[CH3:46])[C:41]([OH:43])=[O:42])(=[O:38])=[O:37])=[CH:32][CH:31]=4)=[CH:28][CH:29]=3)=[O:22])[O:20][C:16]=2[CH:15]=[CH:14][CH:13]=1.[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49]

Participants

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chloride

HCID 59788403(S)-2-(4'-{[4-(2-tert-butoxycarbonylamino-ethoxy)-3-methyl-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-3-methyl-butyric acid2×

Product 2

HCID 6422Trifluoroacetic acid

HCID 59788405(S)-2-(4'-{[4-(2-amino-ethoxy)-3-methyl-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-3-methyl-butyric acid

Procedure

The product of Example 177, (S)-2-(4′-{[4-(2-tert-butoxycarbonylamino-ethoxy)-3-methyl-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-3-methyl-butyric acid, was treated with 40% TFA/methylene chloride solution at ambient temperature for four hours to afford (S)-2-(4′-{[4-(2-amino-ethoxy)-3-methyl-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-3-methyl-butyric acid as a brown solid (TFA salt). MS: calc'd for {M−H]−: 564.65. Found: 564.51.

Sources & evidence

ORD record: ord-41c9ace703504f7998f05e5dffdef98a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

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