(S)-1-((E)-3-{4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acryloyl)-pyrrolidine-2-carboxylic acid tert-butyl ester → (S)-1-((E)-3-{4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acryloyl)-pyrrolidine-2-carboxylic acid

HRID 81367Notes

Reaction equation

HRID 81367 reaction equation
C([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:39])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:23][C:24]3[N:25]=[C:26]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[F:38])[N:27]=[CH:28][C:29]=3[N:30]=2)=[CH:18][CH:17]=1)=[O:7])(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[F:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[O:31][C:26]1[N:27]=[CH:28][C:29]2[N:30]=[C:22]([C:19]3[CH:20]=[CH:21][C:16](/[CH:15]=[CH:14]/[C:13]([N:9]4[CH2:10][CH2:11][CH2:12][C@H:8]4[C:6]([OH:7])=[O:5])=[O:39])=[CH:17][CH:18]=3)[O:23][C:24]=2[N:25]=1

Participants

4

Reactant 1

HCID 86679072(S)-1-((E)-3-{4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acryloyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 53311285(S)-1-((E)-3-{4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acryloyl)-pyrrolidine-2-carboxylic acidYield 75.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 55 mg (S)-1-((E)-3-{4-[5-(2-fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acryloyl)-pyrrolidine-2-carboxylic acid tert-butyl ester in 2 ml of dichloromethane and 1 ml trifluoroacetic acid was stirred at room temperature for 1 h. Then the mixture was concentrated in vacuo and freeze-dried. 37 mg of the title compound were obtained.

Workup

  1. concentrationThen the mixture was concentrated in vacuo
  2. customfreeze-dried

Sources & evidence

ORD record
ord-b07b9a81d1834958940d213cafabb358
Source dataset
uspto-grants-2014_09
Patent number
US08846690B2

Reaction notes

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