HCID 178513293, compound → HCID 23509940, compound

HRID 1883486Notes

Reaction equation

HRID 1883486 reaction equation
[CH:1]1([CH:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=[NH:32])[NH:30]O)=[CH:25][CH:24]=2)[C:8]([N:10]([CH2:18][C:19]([OH:21])=[O:20])[CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(=O)C.[Pd]>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]([N:10]([CH2:18][C:19]([OH:21])=[O:20])[CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:9])=[CH:28][CH:27]=1)(=[NH:30])[NH2:32]

Participants

4

Reactant 1

HCID 178513293HCID 178513293, compound

Product 1

HCID 23509940HCID 23509940, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

({2-(R,S)-Cyclohexyl-3-[4-(N-hydroxycarbamimidoyl)-phenyl]-propionyl}-cyclohexylmethyl-amino)-acetic acid (1.5 g, 3.38 mmol) was dissolved in acetic acid (40 ml). After addition of palladium on charcoal (10%, 100 mg), hydroxgen was bubbled in the reaction mixture at 50°C. for 8 hours. The catalyst was filtered off and washed with acetic acid. The filtrate was evaporated, the residue dissolved in water, lyophilized and purified by chromatography on Sephadex LH20 employing n-butanol (17): glacial acetic acid (1): water (2) was eluent. Pure fractions were combined. The solvent was evaporated, the residue was taken up in water, and the aqueous solution was lyophilized. Yield: 190 mg (13%), MS m/z 428.4 (M+H)+.

Workup

  1. customwas bubbled in the reaction mixture at 50°C. for 8 hours
  2. filtrationThe catalyst was filtered off
  3. washwashed with acetic acid
  4. customThe filtrate was evaporated
  5. dissolutionthe residue dissolved in water
  6. custompurified by chromatography on Sephadex
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9c97c10aa342422595f4729a72a525bd
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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