N-Methylbutylamine → Methyl 5-[(N-methyl-N-butylamino)carbonyl]-2,4-bisbenzyloxybenzoate

HRID 1927697Notes

Reaction equation

HRID 1927697 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16](Br)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C]=[O:29].[CH2:30]([N:32]([CH2:35]C)[CH2:33][CH3:34])C.CNCC[CH2:41][CH3:42]>C1COCC1>[CH3:35][N:32]([C:30]([C:16]1[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:29])[CH2:33][CH2:34][CH2:41][CH3:42]

Participants

6

Reactant 4

HCID 8068N-MethylbutylamineHCID 8471TriethylamineHCID 59317108Methyl 5-bromo-2,4-dibenzyloxybenzoateHCID 178418416HCID 178418416, compound

Product 1

HCID 59614016Methyl 5-[(N-methyl-N-butylamino)carbonyl]-2,4-bisbenzyloxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

a solution of 55.3 g (129.4 mmol) of methyl 2,4-bisbenzyloxy-5-bromobenzoate, 2.1 g (2.6 mmol) of (1,1′-bis(diphenylphosphino)ferrocene)palladium(11) chloride, 2.9 l of carbon monoxide, 17.7 g (101.2 mmol) of triethylamine, 13.8 g (155.2 mmol) of N-methylbutylamine in 1 l of THF is treated in an autoclave for 20 h at 120° C. and 5-10 bar. The resultant solution is subsequently evaporated and crystallised from ethanol. 59 g (98%) of methyl 5-[(N-methyl-N-butylamino)carbonyl]-2,4-bisbenzyloxybenzoate; MW 461.6.

Workup

  1. customThe resultant solution is subsequently evaporated
  2. customcrystallised from ethanol

Sources & evidence

ORD record
ord-3de13dd19c9941caa321faadd5708187
Source dataset
uspto-grants-2012_05
Patent number
US08183279B2

Reaction notes

Loading…