1,2-Dichloroethane → Ethyl 3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoate
Reaction equation
[CH:1]1C=CC2N(O)N=NC=2[CH:6]=1.CCN(CC)CC.[C:18]([O:22][C:23]([NH:25][CH:26]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:27]([OH:31])[C:28]([OH:30])=[O:29])=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(N)CC1.C(Cl)CCl>C(Cl)Cl>[C:18]([O:22][C:23]([NH:25][CH:26]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH:27]([OH:31])[C:28]([O:30][CH2:1][CH3:6])=[O:29])=[O:24])([CH3:21])([CH3:19])[CH3:20]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
74.2 Tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamate EDC (8.3 g, 43.3 mmol), HOBT (6.6 g, 43.1 mmol) and Et3N (7 ml, 50.2 mmol) were added to a mixture of 3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid (10.6 g, 35.9 mmol) and cyclopropylamine (3.3 ml, 47.6 mmol) in DCM (300 mL) at 5° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. After cooling to 5° C. more cyclopropylamine (2 ml, 28.5 mmol), EDC (5 g, 26.1 mmol), HOBT (4 g, 26.1 mmol) and Et3N (3.5 ml, 25.1 mmol) were added, the mixture was allowed to warm to room temperature and the stirring was continued overnight. DCM (300 mL) was added, followed by washing with 0.5 M aqueous HCl solution, brine and drying with MgSO4. The crude product was recrystallized from methyl-tert-butylether, the crystals obtained were washed with n-pentane and dried providing the title compound (10.2 g, 85%).
Workup
- additionwere added
- temperatureto warm to room temperature
- waitthe stirring was continued overnight
- washby washing with 0.5 M aqueous HCl solution, brine
- dry with materialdrying with MgSO4
- customThe crude product was recrystallized from methyl-tert-butylether
- customthe crystals obtained
- washwere washed with n-pentane
- customdried
Sources & evidence
- ORD record
- ord-310840171c074fada23db26edd44e120
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08236798B2
Reaction notes
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