Boron Trichloride → HCID 117875279, compound

HRID 2283437Notes

Reaction equation

HRID 2283437 reaction equation
B(Cl)(Cl)Cl.C([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:21]2[C:22]([F:39])=[C:23]([C@H:28]([NH:31]C(=O)OC(C)(C)C)[CH2:29][CH3:30])[CH:24]=[CH:25][C:26]=2[Cl:27])=[O:20])=[CH:15][CH:14]=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:31][CH:28]([C:23]1[C:22]([F:39])=[C:21]([C:19]([C:16]2[CH:15]=[CH:14][C:13]([OH:12])=[CH:18][CH:17]=2)=[O:20])[C:26]([Cl:27])=[CH:25][CH:24]=1)[CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 89544836HCID 89544836, compound

Product 1

HCID 117875279HCID 117875279, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 3 Boron trichloride (1M in dichloromethane, 10 ml) was added to a solution of tert-butyl N-[(1R)-1-(3-{[4-(benzyloxy)phenyl]carbonyl}-4-chloro-2-fluorophenyl)propyl]carbamate (1.53 g, 3.07 mmol) in dichloromethane (50 ml) in an ice/water bath. The mixture was stirred for 30 minutes then the reaction mixture was poured onto ice/water. The aqueous was basified with saturated sodium bicarbonate and then extracted with dichloromethane (×2). The organic liquors were concentrated and then treated with 2N hydrochloric acid in ethyl acetate to remove protecting group. The residue was concentrated and re-concentrated from ethyl acetate. A solid was obtained from ethyl acetate/diethyl ether mixtures which was isolated by filtration and dried in a vacuum oven to furnish the title compound as an off-white solid (481 mg).

Workup

  1. additionthe reaction mixture was poured onto ice/water
  2. extractionextracted with dichloromethane (×2)
  3. concentrationThe organic liquors were concentrated
  4. additiontreated with 2N hydrochloric acid in ethyl acetate
  5. customto remove
  6. concentrationThe residue was concentrated
  7. concentrationre-concentrated from ethyl acetate
  8. customA solid was obtained from ethyl acetate/diethyl ether mixtures which
  9. customwas isolated by filtration
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-6001bd4208984e829878e896e63a552d
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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