Trifluoroacetic acid → 5-[4-[5-(2,6-Difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]hexahydropyrrolo[3,4-c]pyrrole

HRID 75185Notes

Reaction equation

HRID 75185 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]1[O:13][N:12]=[C:11]([C:14]2[N:15]=[C:16]([N:19]3[CH2:23][CH:22]4[CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][CH:21]4[CH2:20]3)[S:17][CH:18]=2)[CH2:10]1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]1[O:13][N:12]=[C:11]([C:14]2[N:15]=[C:16]([N:19]3[CH2:20][CH:21]4[CH2:26][NH:25][CH2:24][CH:22]4[CH2:23]3)[S:17][CH:18]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673413561,1-dimethylethyl 5-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]hexahydropyrrolo[3,4-c]pyrrol-2(1H)-carboxylate2×

Product 1

HCID 673224925-[4-[5-(2,6-Difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]hexahydropyrrolo[3,4-c]pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,1-dimethylethyl 5-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]hexahydropyrrolo[3,4-c]pyrrol-2(1H)-carboxylate (i.e. the product of Step C) (0.6 g, 1.26 mmol) in dichloromethane (15 mL) cooled to 0° C. was added trifluoroacetic acid (2 mL, 26.93 mmol). The reaction mixture was allowed to warm to room temperature, stirred for 3 h, and then concentrated under reduced pressure. The resulting material was dissolved in water (50 ml) and basified by the addition of sodium hydroxide (10%) to pH 12, and then extracted with chloroform (3×50 mL). The combined organic extracts were concentrated under reduced pressure to provide the title product as a white-gummy solid (0.42 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting material was dissolved in water (50 ml)
  3. additionbasified by the addition of sodium hydroxide (10%) to pH 12
  4. extractionextracted with chloroform (3×50 mL)
  5. concentrationThe combined organic extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-257ebcf3a1654aca9c8f159e63aa4a1b
Source dataset
uspto-grants-2014_09
Patent number
US08835427B2

Reaction notes

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