1,2-Dichloroethane → (R)-benzyl 1-(4,4-diethoxybutylamino)-3-mercapto-3-methyl-1-oxobutan-2-ylcarbamate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:16]([SH:19])([CH3:18])[CH3:17])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH2:34]([O:36][CH:37]([O:42][CH2:43][CH3:44])[CH2:38][CH2:39][CH2:40][NH2:41])[CH3:35]>C(Cl)Cl>[CH2:43]([O:42][CH:37]([O:36][CH2:34][CH3:35])[CH2:38][CH2:39][CH2:40][NH:41][C:13](=[O:15])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:16]([SH:19])([CH3:18])[CH3:17])[CH3:44]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a round bottom flask was added (R)-2-(benzyloxycarbonylamino)-3-mercapto-3-methylbutanoic acid (4.68 g, 16.52 mmol), HOBT (2.53 g, 16.52 mmol), EDC (3.17 g, 16.52 mmol), DCM (50 mL), TEA (2.302 mL, 16.52 mmol) and 4,4-diethoxybutan-1-amine (2.66 g, 16.52 mmol). The reaction was stirred at rt overnight. The reaction was diluted with DCM (150 mL). The organics was washed with water (2×150 mL), saturated aqueous NaCl (100 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give (R)-benzyl 1-(4,4-diethoxybutylamino)-3-mercapto-3-methyl-1-oxobutan-2-ylcarbamate (6.90 gm, 16.2 mmol, 98% yield) as an oil.
Workup
- washThe organics was washed with water (2×150 mL), saturated aqueous NaCl (100 mL)
- customThe organic layer was separated
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6a84eee9b2cd4e949a7c583343b4af4e
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346852B2
Reaction notes
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