HCID 178506508, compound → HCID 86583530, compound

HRID 1016750Notes

Reaction equation

HRID 1016750 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][C:7]=1[CH:15]([NH:21][C:22]1[CH:27]=[CH:26][C:25](/[C:28](=[N:31]/[H])/[NH:29]O)=[CH:24][CH:23]=1)[C:16]([O:18][CH2:19]C)=[O:17])(=[O:3])[NH2:2]>CO.C(O)(=O)C.[Ni]>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([NH:21][CH:15]([C:7]2[CH:8]=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=[CH:11][C:6]=2[O:5][CH2:4][C:1](=[O:3])[NH2:2])[C:16]([O:18][CH3:19])=[O:17])=[CH:27][CH:26]=1)(=[NH:29])[NH2:31]

Participants

4

Reactant 1

HCID 178506508HCID 178506508, compound

Product 1

HCID 86583530HCID 86583530, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

305 mg of ethyl (Z)-(RS)-(2-carbamoylmethoxy-5-ethoxy-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetate were treated in 8 ml of methanol-acetic acid (1:1) with Raney-nickel and stirred under hydrogen. The reaction mixture was filtered, evaporated in a vacuum and, for purification, the residue was triturated in acetonitrile. There were obtained 265 mg of methyl (RS)-(4-carbamimidoyl-phenylamino)-(2-carbamoylmethoxy-5-ethoxyphenyl)-acetate; m.p. 200° C. (dec.), MS: 401 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in a vacuum and, for purification
  3. customthe residue was triturated in acetonitrile

Sources & evidence

ORD record
ord-6999a72288434f35b3efd6b0f43e9cf0
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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