Boron trifluoride etherate → HCID 86619525, compound

HRID 1663424Notes

Reaction equation

HRID 1663424 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:20]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].B(F)(F)F.CCOCC.[OH-].[Na+]>C(Cl)Cl.C(O)(=O)C>[NH2:20][C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:18])[CH3:16]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 86619526HCID 86619526, compound

Product 1

HCID 86619525HCID 86619525, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (2S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-(tritylamino)propylcarbamate (6.19 g, 11.3 mmol) was dissolved in 115 mL of anhydrous CH2Cl2 and 18.2 mL of glacial acetic acid. The reaction mixture was cooled to 0° C. under an atmosphere of N2 and boron trifluoride diethyl etherate (1.51 mL, 11.9 mmol) was added dropwise over several minutes. After stirring for 5 hours, the reaction mixture was treated with 183 mL of cold, aqueous 10% NaOH solution. The reaction mixture was extracted into 200 mL of a 3:1 chloroform/2-propanol mixture and the layers were separated. The aqueous portion was extracted with two additional portions of the chloroform/2-propanol mixture. The organic phases were combined and dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 5%-10% methanol/CHCl3) gave tert-butyl (2S)-2-amino-3-{[tert-butyl(dimethyl)silyl]oxy}propylcarbamate (3.43 g) as a colorless syrup.

Workup

  1. extractionThe reaction mixture was extracted into 200 mL of a 3:1 chloroform/2-propanol mixture
  2. customthe layers were separated
  3. extractionThe aqueous portion was extracted with two additional portions of the chloroform/2-propanol mixture
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1810206daa84a66ace816c03f11a4a0
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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