Boron Trichloride → HCID 11172974, compound

HRID 722670Notes

Reaction equation

HRID 722670 reaction equation
B(Cl)(Cl)Cl.C([O:12][C@H:13]1[C@H:17]([O:18]CC2C=CC=CC=2)[C@@H:16]([CH2:26][O:27]CC2C=CC=CC=2)[S:15][CH:14]1[N:35]1[CH:42]=[CH:41][C:39]([NH2:40])=[N:38][C:36]1=[O:37])C1C=CC=CC=1>ClCCl>[CH:14]1([N:35]2[CH:42]=[CH:41][C:39]([NH2:40])=[N:38][C:36]2=[O:37])[S:15][C@H:16]([CH2:26][OH:27])[C@@H:17]([OH:18])[C@@H:13]1[OH:12]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 67225287HCID 67225287, compound

Product 1

HCID 11172974HCID 11172974, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of boron trichloride (1 M solution) in dry dichloromethane (7 mL, 7 mmol) cooled to −78° C., was added dropwise over a period of 30 min, a solution of compound 7 (265 mg, 0.5 mmol) in dry dichloromethane (10 mL). Stirring was continued overnight at −20° C. The solvent was removed in vacuo and the residue was coevaporated with dichloromethane (4×20 mL). The residue was neutralized with saturated NaHCO3 (25 mL) and washed with chloroform (15 mL). The aqueous layer was applied to a cation exchange (H+) column and eluted with water to remove salts and then eluted with 1N NH4OH to obtain the desired compound 8 (110 mg, 85%) MS z/e 260(M+H)+.

Workup

  1. additionwas added dropwise over a period of 30 min
  2. customThe solvent was removed in vacuo
  3. washwashed with chloroform (15 mL)
  4. washeluted with water
  5. customto remove salts
  6. washeluted with 1N NH4OH

Sources & evidence

ORD record
ord-c90d4d801b5242cda202e224c84f7abb
Source dataset
uspto-grants-2006_11
Patent number
US07138385B2

Reaction notes

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