Acetic Acid → (R)-N-[[4-(aminocarbonylmethyl)phenyl]methyl]-N2-(diphenylacetyl)-ornithinamide

HRID 1952998Notes

Reaction equation

HRID 1952998 reaction equation
C(O)(=O)C.C(O)C.[NH2:8][C:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20](=[O:52])[C@@H:21]([CH2:38][CH2:39][CH2:40][NH:41]C(OCC2C=CC=CC=2)=O)[NH:22][C:23](=[O:37])[CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:14][CH:13]=1)=[O:10].C>[Pd].CO>[NH2:8][C:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20](=[O:52])[C@@H:21]([CH2:38][CH2:39][CH2:40][NH2:41])[NH:22][C:23](=[O:37])[CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:14][CH:13]=1)=[O:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 297MethaneHCID 702EthanolHCID 131721969HCID 131721969, compound

Product 1

HCID 67614787(R)-N-[[4-(aminocarbonylmethyl)phenyl]methyl]-N2-(diphenylacetyl)-ornithinamideYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Prepared analogously to Example 1d) but using a mixture of glacial acetic acid and ethanol (1/1, v/v) as solvent instead of methanol, from (R)-N-[[4-(aminocarbonylmethyl)phenyl]methyl]-N2 -(diphenylacetyl)-N5 -(phenylmethoxycarbonyl)-ornithinamide by catalytic hydrogenation in the presence of palladium on animal charcoal in a yield of 82% of theory. Colourless amorphous substance.

Workup

  1. customPrepared analogously to Example 1d) but

Sources & evidence

ORD record
ord-d22255ef9daf47f7b03dc8f0b5ba2791
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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