{4-[4-(3-tert-Butoxycarbonylamino-3-carbamoylpropoxy)phenyl]butyl}carbamic acid benzyl ester → {3-[4-(4-Aminobutyl)phenoxy]-1-carbamoylpropyl}carbamic acid tert-butyl ester

HRID 254362Notes

Reaction equation

HRID 254362 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH:24]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:25](=[O:27])[NH2:26])=[CH:17][CH:16]=1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO.ClCCl>[C:32]([O:31][C:29](=[O:30])[NH:28][CH:24]([C:25](=[O:27])[NH2:26])[CH2:23][CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH2:10])=[CH:20][CH:19]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 1

HCID 59750592{4-[4-(3-tert-Butoxycarbonylamino-3-carbamoylpropoxy)phenyl]butyl}carbamic acid benzyl ester

Product 1

HCID 66849495{3-[4-(4-Aminobutyl)phenoxy]-1-carbamoylpropyl}carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-Cbz amide 110 (436 mg, 0.873 mmol) and Pearlman's catalyst (100 mg) in methanol (10 mL) and dichloromethane (10 mL) was stirred under atmospheric hydrogen for 18 h. Catalyst was removed by suction filtration over Celite and the filtrate was concentrated to give a colorless oil (318 mg, 100% crude yield). Crude product 120 was used for next step without further purification. m/z (ESI) 366 [C19H31N3O4+H]+.

Workup

  1. customCatalyst was removed by suction filtration over Celite
  2. concentrationthe filtrate was concentrated
  3. customto give a colorless oil (318 mg, 100% crude yield)
  4. customCrude product 120 was used for next step without further purification

Sources & evidence

ORD record
ord-de88cd79eb1942efb1c46d535ade65c8
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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