Trifluoroacetic acid → HCID 69360963, compound

HRID 427573Notes

Reaction equation

HRID 427573 reaction equation
[C:1]([C:5]1[CH:49]=[CH:48][C:8]([C:9]([NH:11][C:12]2[CH:28]=[C:27]([NH:29][C:30](=[O:47])[C@H:31]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[NH:32]C(OC(C)(C)C)=O)[CH:26]=[CH:25][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53]>C(Cl)Cl>[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[CH:28]=[C:27]([NH:29][C:30](=[O:47])[C@H:31]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[NH2:32])[CH:26]=[CH:25][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[O:15])=[O:10])=[CH:48][CH:49]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 54395470HCID 54395470, compound

Product 1

HCID 69360963HCID 69360963, compoundYield 124.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-tert-butylbenzoylamino)-4-[[N-(tert-butyloxycarbonyl)-L-phenylalanyl]amino]-N-(4-methoxyphenyl)benzamide (112 mg, 0.17 mmol) in methylene chloride (5 mL) was added trifluoroacetic acid (0.065 mL, 0.84 mmol). After 1.5 h, an additional portion of trifluoroacetic acid (0.50 mL, 6.5 mmol) was added and the resulting mixture stirred for 1 h. The mixture was concentrated in vacuo to give 144 mg (100%) of the title compound as a tan solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-79fd5667080949a584da5514e4739d9c
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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