Boron trifluoride etherate → Methyl N-[(benzyloxy)carbonyl]-O-{(1S)-2-[(tert-butoxycarbonyl) (cyclopropylmethyl)amino]-1-phenylethyl}-D-serinate

HRID 20123Notes

Reaction equation

HRID 20123 reaction equation
B(F)(F)F.CCOCC.[CH:10]1([CH2:13][N:14]([CH2:22][C@@H:23]([OH:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][CH2:11]1.[N:31]1([C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])[CH2:33][C@@H:32]1[C:34]([O:36][CH3:37])=[O:35]>C(Cl)(Cl)Cl>[CH2:41]([O:40][C:38]([NH:31][C@@H:32]([C:34]([O:36][CH3:37])=[O:35])[CH2:33][O:30][C@@H:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:22][N:14]([C:15]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:21])[CH2:13][CH:10]1[CH2:12][CH2:11]1)=[O:39])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12344749154632-86-7HCID 66939349tert-Butyl [(cyclopropylmethyl)((2S)-2-hydroxy-2-phenylethyl)]carbamate

Product 1

HCID 66939283Methyl N-[(benzyloxy)carbonyl]-O-{(1S)-2-[(tert-butoxycarbonyl) (cyclopropylmethyl)amino]-1-phenylethyl}-D-serinateYield 27.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Boron trifluoride diethyl etherate (0.10 mL, 0.84 mmol) was added to a solution of tert-butyl cyclopropylmethyl[(2S)-2-hydroxy-2-phenylethyl]carbamate (2.45 g, 8.39 mmol) and 1-benzyl 2-methyl (2R)-aziridine-1,2-dicarboxylate (1.97 g, 8.39 mmol) in chloroform (20 mL). After 3 h, the reaction was concentrated. Purification by silica gel chromatography (100% hexanes→30% ethyl acetate/hexanes) gave the title compound (1.21 g).

Workup

  1. concentrationthe reaction was concentrated
  2. customPurification by silica gel chromatography (100% hexanes→30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5b841593848844df94435d334de285f5
Source dataset
uspto-grants-2010_06
Patent number
US07745427B2

Reaction notes

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