Hydrogen Bromide → HCID 20586041, compound
Reaction equation
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN1CC[O:24][CH2:23][CH2:22]1.ClC(OCC(C)C)=O.[BrH:35]>C1COCC1>[Br:35][CH2:22][C:23]([C:17](=[O:19])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])=[O:24]Participants
6
Conditions
- Temperature
- -40 °C
Procedure
N-Cbz-L-leucine (2.10 g, 7.6 mmol) was dissolved in THF (10 mL), cooled to -40° C., and 4-methylmorpholine (0.77 g, 7.6 mmol, 0.83 mL) was added followed by dropwise addition of isobutyl chloroformate (1.04 g, 7.6 mmol, 0.98 mL). After 15 min, the solution was filtered into the previously prepared 0° C. solution of ethereal diazomethane. The resulting solution was allowed to stand at 0° C. for 23 h. HBr (30% in acetic acid) (45.2 mmol, 9 mL) was added and the resulting solution was stirred at 0° C. for 5 min, then washed sequentially with 0.1 N HCl, saturated aqueous NaHCO3 and saturated brine, then dried (MgSO4), filtered and concentrated to give the title compound as a colorless oil (2.43 g, 94%).
Workup
- filtrationthe solution was filtered into the previously prepared 0° C. solution of ethereal diazomethane
- waitto stand at 0° C. for 23 h
- washwashed sequentially with 0.1 N HCl, saturated aqueous NaHCO3 and saturated brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-79650570a04f4b9b8c8a6b5d45ab925a
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998470
Reaction notes
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