HCID 56974531, compound → HCID 21356686, compound

HRID 1167263Notes

Reaction equation

HRID 1167263 reaction equation
C(OC(=O)[N:10]([CH2:32][C:33]([CH3:39])([CH3:38])[CH2:34][CH2:35][C:36]#[N:37])[CH2:11][C@@H:12]([OH:31])[C@@H:13]([NH:21][C:22]([O:24][CH:25]1[CH2:30][O:29][CH2:28][O:27][CH2:26]1)=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.[Pd]>[O:27]1[CH2:26][CH:25]([O:24][C:22](=[O:23])[NH:21][C@@H:13]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@H:12]([OH:31])[CH2:11][NH:10][CH2:32][C:33]([CH3:39])([CH3:38])[CH2:34][CH2:35][C:36]#[N:37])[CH2:30][O:29][CH2:28]1

Participants

5

Reactant 2

HCID 56974531HCID 56974531, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21356686HCID 21356686, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (4-Cyano-2,2-dimethyl-butyl)-[(2R,3S)-3-([1,3]dioxan-5-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-carbamic acid benzyl ester (0.420 g, 0.76 mmol) in EtOAc at ambient temperature was treated with palladium on carbon (0.050 g) and stirred under a balloon of hydrogen. After stirring 16 h the mixture was filtered and solvent was removed in vacuo to give desired product as a colorless oil.

Workup

  1. filtrationwas filtered
  2. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-0b33e0a2cc6845318a8c8384bc5b3081
Source dataset
uspto-grants-2003_09
Patent number
US06617350B2

Reaction notes

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