Methanol → Ethyl N-({[3-(4-{[6-(acetyloxy)hexyl]oxy}butyl)phenyl]amino}carbonyl)glycinate

HRID 857090Notes

Reaction equation

HRID 857090 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1)(=[O:3])[CH3:2].[N:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:24]=[O:25].CO>C(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[C:18]([NH:22][C:24]([NH:23][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:25])[CH:19]=[CH:20][CH:21]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 76283Ethyl isocyanatoacetateHCID 218672196-[4-(3-Aminophenyl)butoxy]hexyl acetate

Product 1

HCID 21867037Ethyl N-({[3-(4-{[6-(acetyloxy)hexyl]oxy}butyl)phenyl]amino}carbonyl)glycinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-[4-(3-Aminophenyl)butoxy]hexyl acetate (2.84 g) in CH2Cl2 (30 ml) was treated with ethyl isocyanatoacetate (1.2 ml). After 0.75 h the mixture was treated with MeOH (2 ml) and stirred for 0.5 h. The mixture was concentrated, purified on a 10 g silica Bond Elut cartridge eluting with Et2O-petroleum ether(1:1) and then with Et2O to give the title compound (3.33 g) ES+ve 437 (MH)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified on a 10 g silica Bond Elut cartridge
  3. washeluting with Et2O-petroleum ether(1:1)

Sources & evidence

ORD record
ord-a19b952348c64046a0a785ab6a618e4c
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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