methyl (Z)-2-[(benzyloxy)carbonyl]amino-3-(3-[(tert-butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-propenoate → Methyl 2-amino-3-(3-[(tert-butoxycarbonyl)amino]methyl-4-methoxyphenyl)propanoate

HRID 1816626Notes

Reaction equation

HRID 1816626 reaction equation
C(OC([NH:11]/[C:12](=[CH:17]\[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:19]=1)/[C:13]([O:15][CH3:16])=[O:14])=O)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[NH2:11][CH:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 2

HCID 58912011methyl (Z)-2-[(benzyloxy)carbonyl]amino-3-(3-[(tert-butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-propenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 22494331Methyl 2-amino-3-(3-[(tert-butoxycarbonyl)amino]methyl-4-methoxyphenyl)propanoateYield 94.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

5 g of methyl (Z)-2-[(benzyloxy)carbonyl]amino-3-(3-[(tert-butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-propenoate was dissolved in methanol. 0.7 g of 10% palladium-carbon was added thereto, followed by stirring for 16 hours in a hydrogen atmosphere. The reaction solution was filtered and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate), to give 3.4 g of methyl 2-amino-3-(3-[(tert-butoxycarbonyl)amino]methyl-4-methoxyphenyl)propanoate was obtained.

Workup

  1. filtrationThe reaction solution was filtered
  2. customevaporated
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-65059bbd528c479d8fc73c1f327aa2b4
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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