Trifluoroacetate → HCID 76605061, compound

HRID 1893650Notes

Reaction equation

HRID 1893650 reaction equation
FC(F)(F)C([O-])=O.[C:8]([O:12][C:13]([N:15]1[CH2:19][CH:18]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=3)[CH:24]=[CH:23][N:22]=2)[CH2:17][CH:16]1[C:33](=[O:50])[NH:34][C:35]1([C:40]([NH:42][S:43]([O:46][CH:47]2[CH2:49][CH2:48]2)(=[O:45])=[O:44])=[O:41])[CH2:37][CH:36]1[CH:38]=[CH2:39])=[O:14])([CH3:11])([CH3:10])[CH3:9]>CCOC(C)=O.CCO>[C:8]([O:12][C:13]([N:15]1[CH2:19][CH:18]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=3)[CH:24]=[CH:23][N:22]=2)[CH2:17][CH:16]1[C:33](=[O:50])[NH:34][C:35]1([C:40]([NH:42][S:43]([O:46][CH:47]2[CH2:49][CH2:48]2)(=[O:44])=[O:45])=[O:41])[CH2:37][CH:36]1[CH2:38][CH3:39])=[O:14])([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 84468TrifluoroacetateHCID 76604921HCID 76604921, compound

Product 1

HCID 76605061HCID 76605061, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the trifluoroacetate salt of 2-(1-cyclopropoxysulfonylaminocarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(6-methoxy-isoquinolin-1-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (181 mg, 0.253 mmol) Rh/AlO3 (37.2 mg, 5 wt %) was added and the mixture was suspended in EtOAc (4.5 mL) and EtOH (1.0 mL). The reaction flask was flushed with H2 gas and the reaction was allowed to stir at room temperature under a hydrogen atmosphere for 3 h. The reaction was filtered through a syringe tip filter (0.45 μM) and washed with ethanol. The filtrate was concentrated and then filtered through a C-18 RP SPE column (Phenomenex Strata, 1 g) and washed with methanol. The filtrate was concentrated and purified on silica (12 g, 0-7% MeOH/CH2Cl2) to give 2-(1-cyclopropoxysulfonylaminocarbonyl-2-ethyl-cyclopropylcarbamoyl)-4-(6-methoxy-isoquinolin-1-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (151 mg, 83%). LCMS found 619.1 [M+H]+.

Workup

  1. customThe reaction flask was flushed with H2 gas
  2. filtrationThe reaction was filtered through a syringe tip
  3. filtrationfilter (0.45 μM)
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated
  6. filtrationfiltered through a C-18 RP SPE column (Phenomenex Strata, 1 g)
  7. washwashed with methanol
  8. concentrationThe filtrate was concentrated
  9. custompurified on silica (12 g, 0-7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-445a7cff15f542e69f7ec98242a67a67
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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