Hydrochloric Acid → HCID 68983197, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C@H:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]([CH3:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.C(N)CN.Cl>CN(C=O)C.C(Cl)Cl>[CH2:19]([N:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)[C@H:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]([CH3:13])[CH3:12])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
Ethyl N-(3-chloro-4-fluorophenyl)valinate (8-1, 0.20 g, 0.74 mmol), benzylbromide (0.380 g, 2.21 mmol), and diisopropylethyleneamine (0.11 g, 0.89 mmol) were combined in DMF (0.1 mL) and stirred 18 h at 50° C. Additional benzylbromide (0.43 g, 2.5 mmol) and diisopropylethylamine (0.22 g, 1.7 mmol) were added and mixture was heated to 60° C. for 4 h and then 50° C. for 18 h. Ethylenediamine (0.266 g, 4.43 mmol) and CH2Cl2 (9 mL) were added to the mixture which stirred for 18 h at 23° C. The mixture was acidified with 1N aqueous HCl. The aqueous layer was washed with CH2Cl2 (3×). The organic layers were dried with MgSO4 and concentrated to give crude ethyl N-benzyl-N-(3-chloro-4-fluorophenyl)valinate (8-2) as a brown oil. MS 364.4 found, 364.1 (M+H+) required.
Workup
- temperaturemixture was heated to 60° C. for 4 h
- wait50° C. for 18 h
- stirringstirred for 18 h at 23° C
- washThe aqueous layer was washed with CH2Cl2 (3×)
- dry with materialThe organic layers were dried with MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1b2758268e1c4a38a2b6d526909c8732
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608739B2
Reaction notes
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