HCID 70030003, compound → HCID 57066573, compound

HRID 1368348Notes

Reaction equation

HRID 1368348 reaction equation
C([O:8][C:9](=[O:39])[C@@H:10]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:14]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:13]=1)C1C=CC=CC=1>CO.[Pd]>[C:35]([O:34][C:32]([NH:31][C@@H:10]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:14]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:13]=1)[C:9]([OH:39])=[O:8])=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

4

Reactant 1

HCID 70030003HCID 70030003, compound

Product 1

HCID 57066573HCID 57066573, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-2-tert-butoxycarbonylamino-3-(4-ethoxycarbonylmethoxy-3-ethoxycarbonylmethyl-phenyl)-propionic acid benzyl ester (796 mg, 1.46 mmol) in MeOH (8 mL) was added 10% Pd/C (4 mg). The heterogeneous mixture was degassed under reduced pressure and allowed to stir at rt for 18 h under H2. The catalyst was removed by filtration and the filtrate evaporated to dryness to give the product as a colorless foam (515 mg, 78%) Electrospray Mass Spectrum (50/50 acetonitrile/water) m/z 476 (M+Na).

Workup

  1. customThe heterogeneous mixture was degassed under reduced pressure
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-46f3797c2fb448629848bbc04b83f4d4
Source dataset
uspto-grants-2003_06
Patent number
US06573295B2

Reaction notes

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