HCID 71738055, compound → HCID 71738056, compound

HRID 882373Notes

Reaction equation

HRID 882373 reaction equation
[Cl:1][C:2]1[C:3]([F:59])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:56]=[CH:55][C:34]([C:35]([O:37][CH:38]([O:40][C:41](=[O:54])[NH:42][CH2:43][C:44]([O:46]CC3C=CC=CC=3)=[O:45])[CH3:39])=[O:36])=[CH:33][C:32]=2[O:57][CH3:58])=[O:29])[CH:5]=[CH:6][CH:7]=1.[H][H]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[C:3]([F:59])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:25])([CH3:26])[CH3:27])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:56]=[CH:55][C:34]([C:35]([O:37][CH:38]([O:40][C:41]([NH:42][CH2:43][C:44]([OH:46])=[O:45])=[O:54])[CH3:39])=[O:36])=[CH:33][C:32]=2[O:57][CH3:58])=[O:29])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 71738055HCID 71738055, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71738056HCID 71738056, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-(benzyloxy)-2-oxoethylcarbamoyloxy)ethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate (Example 23, 35.8 mg, 0.042 mmol) in ethyl acetate (8 mL) was added 10% palladium on carbon (12 mg). The content was stirred at room temperature under 1 atm of hydrogen for 2 h. Palladium on carbon solids were filtered off and washed with ethyl acetate. The solution was concentrated to give 2-((1-(4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoyloxy)ethoxy)carbonylamino)acetic acid as a white solid (20.6 mg, 61%)). MS (ES+) m/z calcd. for C36H37Cl2F2N4O8 [(M+H)+]: 761, found: 761.

Workup

  1. filtrationPalladium on carbon solids were filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-b45c2bb066cf46aeb5b290f3de13ec04
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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