Boron trifluoride etherate → HCID 67268964, compound

HRID 2386252Notes

Reaction equation

HRID 2386252 reaction equation
[N:1]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3][CH:2]1[C:4]([O:6][CH3:7])=[O:5].[Cl:18][CH2:19][C@H:20]([OH:22])[CH3:21].B(F)(F)F.CCOCC>ClCCl>[CH2:11]([O:10][C:8]([NH:1][C@H:2]([CH2:3][O:22][CH:20]([CH3:21])[CH2:19][Cl:18])[C:4]([O:6][CH3:7])=[O:5])=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4255958154632-86-7HCID 6999046(R)-1-Chloro-2-propanol

Product 1

HCID 67268964HCID 67268964, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL flask was added 1-benzyl 2-methyl aziridine-1,2-dicarboxylate (1 g, 4.25 mmol), dichloromethane (12 mL), (R)-1-Chloro-2-propanol (0.76 mL, 8.50 mmol), and boron trifluoride diethyl etherate (0.05 mL, 0.398 mmol). The mixture was stirred at room temperature for 15 minutes Solvent was removed in vacuo and the residue purified on silica gel eluting with Hexanes-EtOAc (0-50%) to give (R)-methyl 2-(benzyloxycarbonylamino)-3-(1-chloropropan-2-yloxy)propanoate (583 mg, 41%). MS [M+H] found 330.2.

Workup

  1. customwas removed in vacuo
  2. customthe residue purified on silica gel eluting with Hexanes-EtOAc (0-50%)

Sources & evidence

ORD record
ord-3e71f5a5c6cb4dc49e14313492f8ed78
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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