HCID 69701672, compound → HCID 69702611, compound

HRID 1266047Notes

Reaction equation

HRID 1266047 reaction equation
C([O:8][CH2:9][C@H:10]1[C:19]2[NH:18][C:17](=[O:20])[CH:16]=[CH:15][C:14]3=[CH:21][N:22]=[C:23]([C:24]4[CH:29]=[CH:28][C:27]([CH2:30][Cl:31])=[CH:26][CH:25]=4)[N:12]([C:13]=23)[CH2:11]1)C1C=CC=CC=1>C(Cl)Cl>[Cl:31][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]2[N:12]3[CH2:11][C@@H:10]([CH2:9][OH:8])[C:19]4[NH:18][C:17](=[O:20])[CH:16]=[CH:15][C:14]([C:13]=43)=[CH:21][N:22]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 69701672HCID 69701672, compound

Product 1

HCID 69702611HCID 69702611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of intermediate 238b (1.35 g, 3.12 mmol) in 75 mL of CH2Cl2 at 0° C., was added solid boron trichloride dimethylsulfide complex (2.75 g, 15.3 mmol) all at once. The reaction was stirred overnight, allowing to warm to room temperature. The reaction was quenched by addition to 400 mL of pH 7 phosphate buffer and 200 mL Et2O. After stirring overnight, the aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated. The product was used without further purification. Obtained 680 mg (64%) of an off white solid.

Workup

  1. customThe reaction was quenched by addition to 400 mL of pH 7 phosphate buffer and 200 mL Et2O
  2. stirringAfter stirring overnight
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was used without further purification
  8. customObtained 680 mg (64%) of an off white solid

Sources & evidence

ORD record
ord-9f42617e297d46a7ae3337d52e1c0a53
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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