Trifluoroacetic acid → HCID 69895115, compound

HRID 1636126Notes

Reaction equation

C([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:38])[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][C:24]([N:26]2[CH2:30][CH2:29][CH2:28][C@@H:27]2[C:31]([O:33]C(C)(C)C)=[O:32])=[O:25])=[CH:18][CH:17]=1)=[O:7])(C)(C)C.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[C:31]([C@H:27]1[CH2:28][CH2:29][CH2:30][N:26]1[C:24](=[O:25])[CH2:23][NH:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][CH2:14][C:13]([N:9]2[CH2:10][CH2:11][CH2:12][C@@H:8]2[C:6]([OH:7])=[O:5])=[O:38])=[CH:17][CH:18]=1)([OH:33])=[O:32]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 53817941HCID 53817941, compound

Product 1

HCID 69895115HCID 69895115, compoundYield 78%

Procedure

A solution of 168 mg (0.32 mmol) (R)-1-[[4-[2-[(R)-2-tert-butoxycarbonyl-pyrrolidin-1-yl]-2-oxo-ethylamino]-phenylamino]-acetyl]-pyrrolidine-2-carboxylic acid tert-butyl ester in 2 ml trifluoroacetic acid was stirred for 4 h at room temperature. The solvent was removed, the residue suspended in toluene and the solvent removed again to eliminate excess trifluoroacetic acid. The residue was re-suspended in 10 ml ether. The resulting suspension was stirred overnight. Filtration and drying gave 160 mg (78%) of the title compound as a brown foam.

Workup

customThe solvent was removed
customthe solvent removed again
filtrationFiltration
customdrying

Sources & evidence

ORD record: ord-80aae6a55aa447cbb5a3b853818f413a
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06512001B1

Reaction notes

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