tert-Butyl[2-(4-{[(2E)-3-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}prop-2-en-1-yl]oxy}phenyl)ethyl]carbamate → tert-Butyl{2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}carbamate

HRID 1433244Notes

Reaction equation

HRID 1433244 reaction equation
[C:1]([O:5][C:6](=[O:50])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17]/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([O:26]CC3C=CC=CC=3)=[C:22]([C@@H:34]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:35][CH2:36][N:37]([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])[CH:21]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:50])[NH:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([C@@H:34]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:35][CH2:36][N:37]([CH:38]([CH3:39])[CH3:40])[CH:41]([CH3:43])[CH3:42])[CH:21]=2)=[CH:14][CH:15]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 57933229tert-Butyl[2-(4-{[(2E)-3-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}prop-2-en-1-yl]oxy}phenyl)ethyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 57933235tert-Butyl{2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl[2-(4-{[(2E)-3-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}prop-2-en-1-yl]oxy}phenyl)ethyl]carbamate (Preparation 6, 475 mg, 0.70 mmol) was dissolved in ethanol (20 ml) and 10% palladium on carbon (50 mg) added. The reaction was heated to 40° C. under 50 psi of hydrogen for 4 hours. The reaction was cooled to room temperature and filtered through Arbocel™, the filtrate was collected and the solvent removed in vacuo to furnish the title compound as a glass, 400 mg.

Workup

  1. filtrationfiltered through Arbocel™
  2. customthe filtrate was collected
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-98542ed07b9f48ac9409ae4f0a307d03
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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