Cadaverine → 7-Amino-1-tritylsulfanyl-heptan-2-one

HRID 1176838Notes

Reaction equation

HRID 1176838 reaction equation
N[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].C[O:9][C:10](=O)[CH2:11][S:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CO>ClCCl.CO.CCN(CC)CC>[NH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:10](=[O:9])[CH2:11][S:12][C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 273CadaverineHCID 887MethanolHCID 262768Methyl 2-tritylsulfanylacetate

Product 1

HCID 670068517-Amino-1-tritylsulfanyl-heptan-2-oneYield 56%

Reagents, catalysts & solvents 1

HCID 21913430dichloromethane MeOH Et3NSolvent

Procedure

1,5-Diaminopentane (0.75 g, 7.21 mmol) was stirred while tritylsulfanyl-acetic acid methyl ester (2.53 g, 7.27 mmol) was added slowly. The mixture was heated at 100° C. for 2 h while methyl alcohol escaped. The product was isolated by column chromatography (dichloromethane/MeOH/Et3N=10/1/0.1) to provide 7-Amino-1-tritylsulfanyl-heptan-2-one (1.63 g, 54%). 1H NMR (300 MHz, CD3OD) δ 7.42-7.36 (m, 6H), 7.31-7.18 (m, 9H), 3.00 (t, J=6.9 Hz, 2H), 2.60 (t, J=6.9 Hz, 2H), 1.42 (m, 4H), 1.27 (m, 2H). 13C NMR (75 MHz, CD3OD) δ 171.1, 145.8, 130.9, 129.2, 128.2, 68.4, 42.5, 40.8, 37.4, 33.4, 30.1, 25.3.

Workup

  1. additionwas added slowly

Sources & evidence

ORD record
ord-50ee632f238c490593f01fdf40e1f4fc
Source dataset
uspto-grants-2010_11
Patent number
US07842835B2

Reaction notes

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