HCID 67313552, compound → HCID 131729000, compound

HRID 1010882Notes

Reaction equation

HRID 1010882 reaction equation
C(O[C:9](=O)[N:10]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH3:22])=[CH:17][CH:16]=1)=[O:14])C)C1C=CC=CC=1>O1CCCC1.CO.[C].[Pd]>[C:27]([O:26][C:24](=[O:25])[NH:23][C@H:21]([C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH2:12][NH:10][CH3:9])=[CH:20][CH:19]=1)[CH3:22])([CH3:29])([CH3:28])[CH3:30]

Participants

5

Reactant 1

HCID 67313552HCID 67313552, compound

Product 1

HCID 131729000HCID 131729000, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

159 mg of the compound [2-2] was dissolved in a mixed solvent of 4 mL of tetrahydrofuran and 2 mL of methanol, then 48 mg of 10% palladium carbon catalyst was added thereto, and the mixture was further stirred for 2 hours under hydrogen atmosphere. Thereto, 95 mg of 10% palladium carbon catalyst was further added and stirred for 3.5 hours under hydrogen atmosphere. The insolubles were filtered through celite and the filtrate was concentrated under reduced pressure, to obtain tert-butyl{(1S)-1-[4-(N-methylglycyl)phenyl]ethyl}carbamate [2-3] (hereinafter, referred to as the compound [2-3]) as crude and purified products. The compound [2-3] was used in the subsequent reaction without further purification.

Workup

  1. stirringstirred for 3.5 hours under hydrogen atmosphere
  2. filtrationThe insolubles were filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ace09b96cbd6480cb26001bb573d6e38
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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