Triethylamine → 2-Benzyloxycarbamoyl-4-methylpentanoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:6]([OH:8])=O)[CH3:2].[CH2:14](NO)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C=CC2[N:31]([OH:32])N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([C:6](=[O:8])[NH:31][O:32][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:2]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Intermediate (3a) (40.3 g, 214 mmol, 1.0 eq) was dissolved into 800 mL DCM and 900 mL THF and the solution was cooled to 0° C. To this was added benzyl hydroxyl amine (34.2 g, 214 mmol, 1.0 eq) followed by HOBt (28.9 g, 214 mmol, 1.0 eq). The mixture was stirred for 5 minutes, then DCC (44.1 g, 214 mmol, 1.0 eq) was added, followed by triethylamine (33.4 mL, 240 mmol, 1.1 eq). The mixture was warmed to room temperature and stirred overnight. The solid was filtered and the filtrate was concentrated. The material was redissolved in 1000 mL EtOAc and washed with 500 mL 1N HCl, 600 mL saturated aq. bicarbonate, dried over MgSO4, filtered. and evaporated to yield intermediate (3b) (59.3 g) as a semisolid. MS m/z: [M+H+] calcd for C16H23NO4 294.2; found 294.2.
Workup
- temperatureThe mixture was warmed to room temperature
- stirringstirred overnight
- filtrationThe solid was filtered
- concentrationthe filtrate was concentrated
- dissolutionThe material was redissolved in 1000 mL EtOAc
- washwashed with 500 mL 1N HCl, 600 mL saturated aq. bicarbonate
- dry with materialdried over MgSO4
- filtrationfiltered
- customand evaporated
Sources & evidence
- ORD record
- ord-1f4eb9b91c304f3faab11f9d0fe7ec9c
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989484B2
Reaction notes
Loading…