Trifluoroacetic acid → {4-[5-(trans-2-Fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetic acid

HRID 403470Notes

Reaction equation

HRID 403470 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[N:19]=[C:20]([O:29][C@@H:30]4[CH2:35][CH2:34][CH2:33][CH2:32][C@H:31]4[F:36])[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]=3[N:24]=2)=[CH:11][C:10]=1[CH3:37])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:36][C@@H:31]1[CH2:32][CH2:33][CH2:34][CH2:35][C@H:30]1[O:29][C:20]1[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]2[N:24]=[C:16]([C:12]3[CH:11]=[C:10]([CH3:37])[C:9]([O:8][CH2:7][C:6]([OH:38])=[O:5])=[C:14]([CH3:15])[CH:13]=3)[O:17][C:18]=2[N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86679899tert-Butyl {4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetate

Product 1

HCID 53311354{4-[5-(trans-2-Fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetic acidYield 109.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

98 mg of {4-[5-(trans-2-fluoro-cyclohexyloxy)-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-acetic acid tert-butyl ester were dissolved in 3.5 ml of dichloromethane and treated with 1.5 ml of trifluoroacetic acid. After 16 h the mixture was concentrated and freeze-dried. 96 mg of the title compound were obtained.

Workup

  1. concentrationAfter 16 h the mixture was concentrated
  2. customfreeze-dried

Sources & evidence

ORD record
ord-90acd23692d34e17803d40586de6b2a0
Source dataset
uspto-grants-2014_06
Patent number
US08748436B2

Reaction notes

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