Water → HCID 69064282, compound

HRID 1436932Notes

Reaction equation

HRID 1436932 reaction equation
[CH3:1][CH:2]([N:4]([CH2:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C:25]([F:28])([F:27])[F:26])[C@H:5]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1)[CH3:3].ClCCl.O.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>FC(F)(F)C(O)=O.CO>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[CH3:3][CH:2]([N:4]([CH2:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C:25]([F:28])([F:26])[F:27])[C@H:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)[CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 444972Fumaric AcidHCID 86608735HCID 86608735, compound

Product 1

HCID 69064282HCID 69064282, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1,1-dimethylethyl (3S)-3-((1-methylethyl)-{[2-(trifluoromethyl)-5-fluorophenyl]-methyl}amino)-pyrrolidine-1-carboxylate (0.26 g) in a mixture of trifluoroacetic acid (2 mL), dichloromethane (8 mL) and water (0.2 mL) was stirred at room temperature for 3 hours. The reaction mixture was evaporated in vacuo. The crude mixture was taken up in methanol and absorbed onto an SCX-2 ion exchange cartridge. After initially washing with methanol, the product was eluted with 2M methanolic ammonia and the collected fractions evaporated in vacuo. The crude product was taken up in methanol and fumaric acid (1 equiv. ) in methanol added. The solvent was removed in vacuo and the resultant gum triturated with diethyl ether. The solid formed was filtered off and dried in vacuo at 50° C. to yield the title compound as an off-white microcrystalline solid. 1H NMR (300 MHz, CD3OD) δH: 1.09 (d, 3H), 1.10 (d, 3H), 1.87 (m, 1H), 2.15 (m, 1H), 3.01 (m, 2H), 3.23 (m, 1H), 3.38 (m, 2H), 3.81 (m, 1H), 3.91 (s, 2H), 6.70 (s, 2H), 7.15 (dt, 1H), 7.73 (m, 2H); MS: [M+H]=305.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customabsorbed onto an SCX-2 ion exchange cartridge
  3. washAfter initially washing with methanol
  4. washthe product was eluted with 2M methanolic ammonia
  5. customthe collected fractions evaporated in vacuo
  6. customThe solvent was removed in vacuo
  7. customthe resultant gum triturated with diethyl ether
  8. customThe solid formed
  9. filtrationwas filtered off
  10. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-b6a7b3e91f38495e8e6f9ccad02db526
Source dataset
uspto-grants-2009_11
Patent number
US07619096B2

Reaction notes

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