HCID 68856700, compound → HCID 59787401, compound

HRID 1965983Notes

Reaction equation

HRID 1965983 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)=[O:27])=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 68856700HCID 68856700, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59787401HCID 59787401, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-[5-(cyclopentanecarbonyl-amino)-pent-1-enyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine as obtained in the previous step in EtOAc (20 mL) and add 10% Pd/C (Degussa type, 200 mg). Then apply a pressure of 70 psi of hydrogen while shaken vigorously. Filter the crude mixture through a short pad of Celite® and concentrate in vacuo. Purify the resulting material by preparative HPLC to obtain the desired intermediate as a clear oil (311 mg, 87% for the two previous steps). MS (ES+) m/z=485.2 (M+Na)+.

Workup

  1. filtrationFilter the crude mixture through a short pad of Celite®
  2. concentrationconcentrate in vacuo
  3. customPurify the resulting material by preparative HPLC

Sources & evidence

ORD record
ord-1a4e078b608246ac8c7a47442ff3c434
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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