HCID 86625804, compound → HCID 59868565, compound

HRID 1924001Notes

Reaction equation

HRID 1924001 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH2:11]/[C:12](/[NH:19][C:20]([O:22][CH3:23])=[O:21])=[CH:13]/[NH:14][C:15]([O:17][CH3:18])=[O:16])[C:7]([O:9][CH3:10])=[O:8])=[O:4]>C(O)C.[Pd]>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH2:11][CH:12]([NH:19][C:20]([O:22][CH3:23])=[O:21])[CH2:13][NH:14][C:15]([O:17][CH3:18])=[O:16])[C:7]([O:9][CH3:10])=[O:8])=[O:4]

Participants

4

Reactant 1

HCID 86625804HCID 86625804, compound

Product 1

HCID 59868565HCID 59868565, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl (2S,4Z)-2,4,5-tris[(methoxycarbonyl)amino]pent-4-enoate CXXVII (624 mg, 1.87 mmol) in ethanol (15 mL) was added 10% Pd/C catalyst (60 mg). The mixture was placed in an autoclave and exposed to 50 atm of H2 with stirring at r.t. for 36 h. Reaction mixture was filtered through Celite and concentrated to dryness to give crude methyl (2S)-2,4,5-tris[(methoxycarbonyl)amino]pentanoate CXXVIII (540 mg). ESIMS found for C12H21N3O8 m/z 358 (M+Na).

Workup

  1. customReaction mixture
  2. filtrationwas filtered through Celite
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cda276ccc75a4d1f83bb6a59682e3ed5
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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