Trifluoroacetic acid → HCID 69949753, compound

HRID 2268657Notes

Reaction equation

C([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[CH2:13][CH2:14][CH2:15][N:16]([C:24](=[O:49])[C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([O:32][CH2:33][CH2:34][N:35](C(OC(C)(C)C)=O)[C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)[CH:26]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])=[O:7])(C)(C)C.C(OC([C@H]1CCCN1CCCNC1C=CC=CC=1F)=O)(C)(C)C.[F:73][C:74]([F:79])([F:78])[C:75]([OH:77])=[O:76]>>[F:73][C:74]([F:79])([F:78])[C:75]([OH:77])=[O:76].[Cl:31][C:29]1[CH:30]=[C:25]([CH:26]=[C:27]([O:32][CH2:33][CH2:34][NH:35][C:36]2[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=2)[CH:28]=1)[C:24]([N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])[CH2:15][CH2:14][CH2:13][N:9]1[CH2:10][CH2:11][CH2:12][C@@H:8]1[C:6]([OH:7])=[O:5])=[O:49]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 53901664HCID 53901664, compound

HCID 53974262HCID 53974262, compound

Product 1

HCID 69949753HCID 69949753, compound

Procedure

A solution of (R)-1-{3-[{3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoyl}-(2-fluoro-phenyl)-amino]-propyl}-pyrrolidine-2-carboxylic acid tert-butyl ester and (R)-1-[3-(2-fluoro-phenylamino)-propyl]-pyrrolidine-2-carboxylic acid tert butyl ester (0.110 g) in trifluoroacetic acid (5 ml) for 18 h and then the solvent removed under reduced pressure. The residue was subjected to preparative hplc to give the title compound (0.027 g) as a colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-eddfeed9550b422ebfa2475b73e44eff
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326386B1

Reaction notes

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