N,N,N',N'-Tetramethylazodicarboxamide → Benzenepropanol

HRID 10491

Reaction equation

HRID 10491 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][N:20]=[CH:21]2)(=[O:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].N(C(N(C)C)=O)=NC(N(C)C)=O.[C:38]1([CH2:44][CH2:45][CH2:46][OH:47])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]([S:13]([C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][N:20]=[CH:21]2)(=[O:14])=[O:15])[CH2:46][CH2:45][CH2:44][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:38]1([CH2:44][CH2:45][CH2:46][OH:47])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 31234BenzenepropanolHCID 21979958N-(tert-butoxycarbonyl)-N'-[(5-isoquinolyl)sulfonyl]-1,3-propylenediamine

Product 2

HCID 31234BenzenepropanolHCID 21979966N-(tert-butoxycarbonyl)-N'-[(5-isoquinolyl)sulfonyl]-N'-(3-phenylpropyl)-1,3-propylenediamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Intermediate 1 (640 mg), 1,1′-azobis(N,N-dimethylformamide) (1200 mg, Aldrich or prepared according to Chemistry Letters, 539 (1994)) and 3-phenyl-1-propanol (710 μl, Tokyo Kasei Kogyo) in tetrahydrofuran (30 ml) was added with tri(n-butyl)phosphine (1.75 ml, Tokyo Kasei Kogyo) with stirring and ice cooling and stirred at room temperature under argon atmosphere for 13.5 hours. The precipitates in the reaction mixture were removed by filtration, and then the solvent was evaporated from the filtrate under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate mixed solvent) to obtain the title compound (913 mg, mixture with a small amount of 3-phenyl-1-propanol).

Workup

  1. stirringice cooling and stirred at room temperature under argon atmosphere for 13.5 hours
  2. customThe precipitates in the reaction mixture
  3. customwere removed by filtration
  4. customthe solvent was evaporated from the filtrate under reduced pressure
  5. customThe residue was purified by flash column chromatography (hexane/ethyl acetate mixed solvent)

Sources & evidence

ORD record
ord-99be45a0fb164c68b4577c67d8e9e37e
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Linked notes

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