Bicarbonate Ion → HCID 20033706, compound

HRID 231695Notes

Reaction equation

HRID 231695 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][S:12]([C:15]2[S:19][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1.B(Br)(Br)Br.O.C(=O)(O)[O-]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][S:12]([C:15]2[S:19][C:18]([S:20]([NH2:23])(=[O:21])=[O:22])=[CH:17][CH:16]=2)(=[O:13])=[O:14])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 962WaterHCID 25134Boron tribromideHCID 20033664HCID 20033664, compound

Product 1

HCID 20033706HCID 20033706, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of product from Step B, (3.0 g, 8.0 mmol) in CH2Cl2 (132 ml), cooled to -78° C., was added boron tribromide (25.9 ml, 1.0M in CH2Cl2, 25.9 mmol) dropwise and the resulting mixture was stirred at room temperature overnight. The reaction was cooled to 0° C., water and saturated bicarbonate solution added and extracted with ethyl acetate. Drying and solvent evaporation gave a solid (2.9 g); recrystallization from CHCl3 gave the title compound (1.5 g, 52%); m.p. 112°-115° C.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. customDrying
  4. customsolvent evaporation

Sources & evidence

ORD record
ord-9249950b86c541d5853cbe4573ed0c89
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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