Methanol → HCID 20677630, compound

HRID 650673Notes

Reaction equation

HRID 650673 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:40]([CH3:42])[CH3:41])[CH2:10][O:11][C:12](=[O:39])[CH:13]([NH:26][S:27]([C:30]1[C:35]([CH3:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:31]=1[CH3:38])(=[O:29])=[O:28])[CH2:14][NH:15]C(OCC1C=CC=CC=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>[Pd]>[C:1]([O:5][C:6]([NH:8][CH:9]([CH:40]([CH3:42])[CH3:41])[CH2:10][O:11][C:12](=[O:39])[CH:13]([NH:26][S:27]([C:30]1[C:31]([CH3:38])=[CH:32][C:33]([CH3:37])=[CH:34][C:35]=1[CH3:36])(=[O:29])=[O:28])[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 20677631HCID 20677631, compound

Product 1

HCID 20677630HCID 20677630, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a mixture of 3-Benzyloxycarbonylamino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid 2-tert-butoxycarbonylamino-3-methyl-butyl ester (Z-1) (280 mg, 0.46 mmol methanol (70 ml), was added Pd/C. The reaction was stirred under hydrogen atmosphere overnight at room temperature. Catalyst was removed by filtration and the solvent was evaporated. Purification of the residue on silica gel (1:2 hexane:EtOAc) gave 120 mg (56%) of pure 3-Amino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid 2-tert-butoxycarbonylamino-3-methyl-butyl ester (Z-2).

Workup

  1. customCatalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customPurification of the residue on silica gel (1:2 hexane:EtOAc)

Sources & evidence

ORD record
ord-6d7da57d11304650b5548cd276f189c6
Source dataset
uspto-grants-2001_08
Patent number
US06274620B1

Reaction notes

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