Acetic Acid → HCID 67928038, compound

HRID 981418Notes

Reaction equation

HRID 981418 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[CH:12]=[CH:11][C:10]=1[CH2:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:47])[CH2:34][CH2:35][NH:36]C(OCC1C=CC=CC=1)=O)=[O:25])C1C=CC=CC=1.[C:48]([OH:51])(=[O:50])[CH3:49].[H][H].CCOCC>C(O)C.[C].[Pd]>[C:48]([OH:51])(=[O:50])[CH3:49].[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[CH2:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:47])[CH2:34][CH2:35][NH2:36])=[O:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 20071558HCID 20071558, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67928038HCID 67928038, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution (20 ml) of 1-(2,4-dibenzyloxyphenylacetyl)amino-5-(3-benzyloxycarbonylaminopropionyl)aminopentane (440 mg) in ethanol are added 10 % palladiumcarbon (70 mg) and acetic acid (0.01 ml) and catalytic reduction is conducted in a hydrogen stream at room temperature under atmospheric pressure. After four hours, the catalyst is removed by filtration and the filtrate is concentrated under reduced pressure. To the glass-like product obtained is added ether to digest into powder. The resulting product is filtered and dried to yield 1-(2,4-dihydroxyphenylacetyl)amino-5-(3-aminopropionyl)aminopentane acetate (209 mg).

Workup

  1. customthe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customTo the glass-like product obtained
  4. filtrationThe resulting product is filtered
  5. customdried

Sources & evidence

ORD record
ord-cd53575c877f413082c96666c7d56dc0
Source dataset
uspto-grants-1991_02
Patent number
US04990511

Reaction notes

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