Benzyl chloroformate → HCID 15030958, compound

HRID 1844170Notes

Reaction equation

HRID 1844170 reaction equation
Cl.[NH2:2][C@H:3]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:5][CH2:6][CH3:7].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>O.C1COCC1.O>[CH2:22]([O:21][C:19]([NH:2][C@H:3]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:5][CH2:6][CH3:7])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

Product 1

HCID 15030958HCID 15030958, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

12 g (66.1 mmol) of rac-methyl norleucinate hydrochloride were initially charged in 974 ml of water/THF (8:1), and 28.3 g (204.8 mmol) of potassium carbonate were added. The reaction mixture was cooled to 0° C. 12.3 ml (72.7 mmol) of benzyl chloroformate were slowly added dropwise and the reaction mixture was stirred at RT overnight. The mixture was diluted with 480 ml of water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered off and concentrated. The residue was purified by silica gel chromatography (cyclohexane/ethyl acetate=4:1). This gave 18.0 g (97.6% of theory, purity 100%) of the target compound.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. filtrationfiltered off
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (cyclohexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-759615d13ff04960b34a0bf4b9a7278e
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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