Dichloromethane → HCID 86760963, compound
Reaction equation
[C:1]([NH:4][CH:5]([CH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[C:15]([NH2:22])=[C:14]([C:23]([F:26])([F:25])[F:24])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[OH-].[Na+].C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>O.CC(C)=O.CCOC(C)=O>[C:1]([NH:4][C@H:5]([CH2:11][C:12]1[CH:13]=[C:14]([C:23]([F:25])([F:24])[F:26])[C:15]([NH2:22])=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:17]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]Participants
Conditions
- Temperature
- 37 °C
Procedure
4 mL Alcalase 2.4 L FG (Novozymes A/S; DK 2880 Bagsvaerd) was added to a solution of 3.65 g (20.5 mmol) Na2HPO4 dihydrate in 130 mL water warmed to 37° C. and the pH was adjusted to 7.5 by the addition of NaH2PO4 dihydrate. Then a solution of 3.8 g (9.84 mmol) ethyl 2-acetylamino-3-(4-amino-3,5-bis-trifluoromethyl-phenyl)-propionate in 40 mL acetone was added dropwise at 37° C. with stirring. The pH value of the reaction mixture was constantly kept in the range from 7.4-7.6 by the addition of 1 M NaOH. After the addition had ended the mixture was stirred for 4 h at 37° C. After cooling to RT the reaction mixture was combined with 300 mL DCM, 300 mL 15% K2CO3 solution and 200 mL water. The organic phase was separated off, washed with 7% K2CO3 solution and dried over Na2SO4. After the desiccant and solvent had been eliminated the crude product (2.2 g) was further reacted without purification. ESI-MS: (M+H)+387 Rf=0.60 (silica gel, PE/EtOAc 1:1)
Workup
- additionAfter the addition
- stirringwas stirred for 4 h at 37° C
- temperatureAfter cooling to RT the reaction mixture
- customThe organic phase was separated off
- washwashed with 7% K2CO3 solution
- dry with materialdried over Na2SO4
- customwas further reacted without purification
Sources & evidence
- ORD record
- ord-bc787e449bf6431b89f3ca357af15afd
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595312B2
Reaction notes
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