(E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid → HCID 58897684, compound

HRID 12589Notes

Reaction equation

HRID 12589 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:31])([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=1)/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:31])([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=1)[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58897682(E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid

Product 1

HCID 58897684HCID 58897684, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid (53 mg, 0.12 mMol) in AcOEt (10 ml) is added palladium on charcoal (10 mg, 10%). The reaction is stirred under a H2-atmosphere at RT for 17 hours. The reaction mixture is filtered over Celite and the filtrate is concentrated under reduced pressure to give the title compound as a colourless oil. The crude product is sufficiently pure to be used in the next stage without further purification.

Workup

  1. filtrationThe reaction mixture is filtered over Celite
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a9f79f4a19f0430b8d7025cea73829d7
Source dataset
uspto-grants-2010_06
Patent number
US07728020B2

Reaction notes

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