Methanol → HCID 86617194, compound

HRID 1993487Notes

Reaction equation

HRID 1993487 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:7]([O:28]COC)=[CH:8][C:9]2[O:14][C:13]([CH3:16])([CH3:15])[C@@H:12]([OH:17])[C@H:11]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]=2[CH:27]=1)=[O:4].B(Br)(Br)Br.CO.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:7]([OH:28])=[CH:8][C:9]2[O:14][C:13]([CH3:16])([CH3:15])[C@@H:12]([OH:17])[C@H:11]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]=2[CH:27]=1)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 86617192HCID 86617192, compound

Product 1

HCID 86617194HCID 86617194, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-Chloro-N-{(±)-trans-3-hydroxy-7-methoxymethoxy-2,2-dimethyl-4-[(2-phenylethyl)amino]-3,4-dihydro-2H-1-benzopyran-6-yl}-acetamide (228 mg, 0.51 mmol) in methylene chloride (6 mL), boron tribromide (1 M solution in methylene chloride, 2.42 mL, 2.42 mmol) was added at 0° C., and the resulting mixture was stirred for 2 hours. Upon the completion of the reaction, methanol and saturated aqueous sodium hydrogencarbonate aqeuous solution were added thereto, and the resulting solution was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate aqeuous solution and then with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated to obtain the aimed product (yield: 100%).

Workup

  1. additionwere added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogencarbonate aqeuous solution
  4. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5dbd258a856f441eaef872b018e35163
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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