Boron Trichloride → HCID 178429239, compound

HRID 734757Notes

Reaction equation

HRID 734757 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[C:22]3[CH3:28])=[O:17])=[CH:4][C:3]=1[O:29]C.B(Cl)(Cl)Cl>C(Cl)Cl.CCOC(C)=O.O.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[C:22]3[CH3:28])=[O:17])=[CH:4][C:3]=1[OH:29]

Participants

7

Reactant 2

HCID 25135Boron TrichlorideHCID 178487581HCID 178487581, compound

Product 1

HCID 178429239HCID 178429239, compoundYield 20%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
35 °C

Procedure

The product from Example 95 (105 mg, 0.247 mmol, 1.00 equiv) was cooled to −78° C. in 2.0 mL CH2Cl2 and BCl3 (1.0 M in CH2Cl2, 3.70 mL, 3.71 mmol, 15.0 equiv) was added dropwise. The reaction was warmed to 35° C. and stirred for 90 hours. The reaction mixture was diluted with EtOAc and water and basified to pH 14 with 6N NaOH. The phases were separated, and the aqueous phase was acidified to pH 4 with 6N HCl. The precipitate was filtered and washed with Et2O. The residue was purified by reverse-phase HPLC (10-95% CH3CN/H2O, 0.1% TFA over 18 minutes, retention time 9.15 min) to provide 20 mg (20%) of the title compound as a white solid. MS (ES+) m/e 411 [M+H]+

Workup

  1. customThe phases were separated
  2. filtrationThe precipitate was filtered
  3. washwashed with Et2O
  4. customThe residue was purified by reverse-phase HPLC (10-95% CH3CN/H2O, 0.1% TFA over 18 minutes, retention time 9.15 min)

Sources & evidence

ORD record
ord-83805aa26ab6430490b60816c2a7c658
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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