Trifluoroacetic acid → HCID 178512542, compound

HRID 1486895Notes

Reaction equation

C([O:5][C:6]([C:8]1([CH2:53][C:54]([O:56]C(C)(C)C)=[O:55])[O:12][N:11]=[C:10]([C:13]2[CH:18]=[C:17]([O:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH2:30])=[NH:29])=[CH:23][CH:22]=3)[CH:16]=[CH:15][C:14]=2[CH2:32][CH2:33][C:34]([NH:36][C@H:37]([C:46]([O:48]C(C)(C)C)=[O:47])[CH2:38][C:39]([O:41]C(C)(C)C)=[O:40])=[O:35])[CH2:9]1)=[O:7])(C)(C)C.[C:61]([OH:67])([C:63]([F:66])([F:65])[F:64])=[O:62]>>[F:64][C:63]([F:66])([F:65])[C:61]([OH:67])=[O:62].[NH:27]([C:24]1[CH:23]=[CH:22][C:21]([C:20]([O:19][C:17]2[CH:16]=[CH:15][C:14]([CH2:32][CH2:33][C:34]([NH:36][C@H:37]([C:46]([OH:48])=[O:47])[CH2:38][C:39]([OH:41])=[O:40])=[O:35])=[C:13]([C:10]3[CH2:9][C:8]([C:6]([OH:7])=[O:5])([CH2:53][C:54]([OH:56])=[O:55])[O:12][N:11]=3)[CH:18]=2)=[O:31])=[CH:26][CH:25]=1)[C:28]([NH2:30])=[NH:29]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178451088HCID 178451088, compound

Product 1

HCID 178512542HCID 178512542, compound

Procedure

A mixture of di-tert-butyl N-(3-(2-(5-(tert-butoxycarbonyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-((4-carbamimidamidobenzoyl)oxy)phenyl)propanoyl)-L-aspartate (44.6 mg) and TFA (1 mL) was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and then, the residue was washed with diethyl ether to obtain the title compound (25.1 mg).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
washthe residue was washed with diethyl ether

Sources & evidence

ORD record: ord-889d198fe1e446e692dc656d016f7de1
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428470B2

Reaction notes

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