HCID 67637700, compound → HCID 15391045, compound

HRID 342802Notes

Reaction equation

HRID 342802 reaction equation
C([O:8][C:9]([C:11]1[N:12]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([N+:49]([O-])=O)=[CH:45][CH:44]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([CH2:20][CH:21]([N:23]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:24][C@H:25]([OH:34])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:22])=[CH:15][CH:14]=2)=[O:10])C1C=CC=CC=1>C1COCC1.[Pd]>[NH2:49][C:46]1[CH:47]=[CH:48][C:43]([CH2:42][N:12]2[C:13]3[C:18](=[CH:17][C:16]([CH2:20][CH:21]([N:23]([C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])[CH2:24][CH:25]([OH:34])[CH2:26][O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH3:22])=[CH:15][CH:14]=3)[CH:19]=[C:11]2[C:9]([OH:10])=[O:8])=[CH:44][CH:45]=1

Participants

4

Reactant 1

HCID 67637700HCID 67637700, compound

Product 1

HCID 15391045HCID 15391045, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-{2-[tert-butoxycarbonyl-(2(S)-hydroxy-3-phenoxypropyl)-amino]-propyl}-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid benzyl ester (134 mg, 0.19 mmol) in THF (6 ml) was added 14 mg of 10% Pd/C catalyst. The reaction mixture was hydrogenated on a Parr shaker at 45 psi for about 4 hrs and then filtered to remove the catalyst. The filtrate was concentrated under reduced pressure to afford a yellow foam (112 mg), AP-MS 572.

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cd332161991b4145ad3769eb429bc02e
Source dataset
uspto-grants-1999_01
Patent number
US05859044

Reaction notes

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