HCID 90282012, compound → HCID 90281946, compound

HRID 1497504Notes

Reaction equation

HRID 1497504 reaction equation
C(OC([NH:11][C@H:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:16][CH:15]=1)=O)C1C=CC=CC=1>C(O)C.O1CCCC1.[C].[Pd]>[C:23]([O:22][C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C@@H:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH2:11])=[CH:15][CH:16]=1)=[O:21])([CH3:24])([CH3:26])[CH3:25]

Participants

5

Reactant 1

HCID 90282012HCID 90282012, compound

Product 1

HCID 90281946HCID 90281946, compoundYield 107.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-[(benzyloxy)carbonyl]-4-(tert-butoxycarbonyl)-L-phenylalaninate (570 mg) in ethanol (3.00 mL) and tetrahydrofuran (3.00 mL) was added 10% palladium-carbon (138 mg) under an argon atmosphere, and then followed by stirring at room temperature overnight under a hydrogen atmosphere. The reaction suspension was filtered through Celite, and the filtrate was concentrated under reduced pressure to obtain tert-butyl 4-(tert-butoxycarbonyl)-L-phenylalaninate (431 mg).

Workup

  1. filtrationThe reaction suspension was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ba7669862f7f45398fac1c4bd391d97d
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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