tert-Butyl(S)-1-(2-{4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetyl)pyrrolidine-2-carboxylate → (S)-1-(2-{4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetyl)pyrrolidine-2-carboxylic acid

HRID 81510Notes

Reaction equation

HRID 81510 reaction equation
[F:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[O:8][C:9]1[N:10]=[C:11]([O:42][CH2:43][CH2:44][CH3:45])[C:12]2[N:17]=[C:16]([C:18]3[CH:39]=[C:38]([CH3:40])[C:21]([O:22][CH2:23][C:24]([N:26]4[CH2:30][CH2:29][CH2:28][C@H:27]4[C:31]([O:33]C(C)(C)C)=[O:32])=[O:25])=[C:20]([CH3:41])[CH:19]=3)[O:15][C:13]=2[N:14]=1>ClCCl.FC(F)(F)C(O)=O>[F:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[O:8][C:9]1[N:10]=[C:11]([O:42][CH2:43][CH2:44][CH3:45])[C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[C:20]([CH3:41])[C:21]([O:22][CH2:23][C:24]([N:26]4[CH2:30][CH2:29][CH2:28][C@H:27]4[C:31]([OH:33])=[O:32])=[O:25])=[C:38]([CH3:40])[CH:39]=3)[O:15][C:13]=2[N:14]=1

Participants

4

Reactant 1

HCID 86688234tert-Butyl(S)-1-(2-{4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetyl)pyrrolidine-2-carboxylate

Product 1

HCID 53311962(S)-1-(2-{4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetyl)pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

76 mg of tert-butyl(S)-1-(2-{4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetyl)pyrrolidine-2-carboxylate were dissolved in 1.6 ml of dichloromethane and 0.8 ml of trifluoroacetic acid. After 16 h at room temperature, the mixture was concentrated under reduced pressure and freeze-dried. This gave 83 mg of the title compound.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customfreeze-dried

Sources & evidence

ORD record
ord-40b3c824e7ea4134b807badf7b20bd58
Source dataset
uspto-grants-2014_09
Patent number
US08846691B2

Reaction notes

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