Trifluoroacetate → HCID 76605061, compound

HRID 2405800Notes

Reaction equation

HRID 2405800 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-817eea27c4b44b59b2b096946e835353
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

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