Allyl bromide → HCID 57252150, compound
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@:12]([CH2:19][CH:20]([CH3:22])[CH3:21])([CH3:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[CH3:24][CH:25]([N-]C(C)C)[CH3:26].C(Br)C=C>C1COCC1>[CH2:26]([C@@H:13]([C@@:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:25]=[CH2:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -80 °C
Procedure
500 mg (1.71 mmol) of methyl(S)-3-benzyloxycarbonylamino-3-isobutyl-butanoate, prepared according to the procedure described in Liebigs Ann., pp 1217-1228 (1995), is dissolved in 10 mL of dry THF and cooled under Argon to -80° C. 1.881 mL (3.762 mmol) of 2M LDA is added, and the mixture is stirred at -40° C. for 20 minutes. The reaction is cooled to -78° C., and 828 mg (6.84 mmol) of allyl bromide are added. The mixture is stirred at -78° C. for 5 hours and at room temperature overnight. The reaction is quenched with 20 mL of 1M pH 7 phosphate buffer. The pH is lowered to 2 with 1N HCl. The water layer is extracted with EtOAc. The combined organic layers are dried over MgSO4, and concentrated to provide the crude product, which is purified by chromatography using 70% hexanes/30% EtOAc as eluant to give the title compound.
Workup
- temperatureThe reaction is cooled to -78° C.
- stirringThe mixture is stirred at -78° C. for 5 hours and at room temperature overnight
- customThe reaction is quenched with 20 mL of 1M pH 7 phosphate buffer
- extractionThe water layer is extracted with EtOAc
- dry with materialThe combined organic layers are dried over MgSO4
- concentrationconcentrated
- customto provide the crude product, which
- customis purified by chromatography
Sources & evidence
- ORD record
- ord-dbdbb571fe4d47ae9a7be564f4db52fb
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05830869
Reaction notes
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