Trifluoroacetic acid → HCID 86622699, compound

HRID 729634Notes

Reaction equation

HRID 729634 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH:16][C@H:17]3[C@@H:21]([OH:22])[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]>C(Cl)Cl.C1(C)C=CC=CC=1>[OH:36][C:30]([C:32]([F:35])([F:34])[F:33])=[O:31].[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH:16][C@H:17]3[C@@H:21]([OH:22])[CH2:20][NH:19][CH2:18]3)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131727599HCID 131727599, compound

Product 1

HCID 86622699HCID 86622699, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-tert-butyl 3-(2-(3-fluorophenyl)pyrimidine-5-carboxamido)-4-hydroxypyrrolidine-1-carboxylate (1.22 g, 3.03 mmol) in DCM (6 mL) was added TFA (2 mL). The solution stirred at room temperature for 3 hrs and then diluted with toluene (5 mL) and the solvent removed to give a solid, cis-2-(3-fluorophenyl)-N-(4-hydroxypyrrolidin-3-yl)pyrimidine-5-carboxamide-TFA salt (1.26 g, 98%). LC/MS (M+H)=303.1 observed, 303.13 expected.

Workup

  1. customthe solvent removed

Sources & evidence

ORD record
ord-60009e2262ae46c0b863a81598884605
Source dataset
uspto-grants-2009_09
Patent number
US07582643B2

Reaction notes

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