Acetic Acid → HCID 178476430, compound

HRID 52600Notes

Reaction equation

HRID 52600 reaction equation
[NH2:1][C:2](=[N:37][N+]([O-])=O)[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[CH:30][CH:29]=1)=[O:25])[NH:8][C:9](=[O:23])[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:41]([OH:44])(=[O:43])[CH3:42]>[Pd].C(Cl)Cl>[C:17]1([CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]([NH:8][C@@H:7]([C:24]([NH:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH3:36])=[CH:32][CH:33]=2)=[O:25])[CH2:6][CH2:5][CH2:4][NH:3][C:2](=[NH:1])[NH2:37])=[O:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:41]([O-:44])(=[O:43])[CH3:42]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 137231658HCID 137231658, compound

Product 1

HCID 178476430HCID 178476430, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Prepared analogously to Example 1c) from (R)-N5 -[amino(nitroimino)methyl]-N2 -(diphenylacetyl)-N-[(4-ethoxyphenyl)-methyl]-ornithinamide by catalytic hydrogenation in the presence of palladium black and 80% aqueous acetic acid in a yield of 97% of theory. Colourless crystals, mp. 97°-100° C. and Rf 0.75. IR (CH2Cl2): 1665 cm-1 (C=O) 1515 cm-1 (amide-II) ESI-MS: (M+H)+ =502

Sources & evidence

ORD record
ord-0e862e44f6e74abea5a6d656f910cb72
Source dataset
uspto-grants-1997_04
Patent number
US05616620

Reaction notes

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