Methanol → HCID 86617194, compound

HRID 2425364Notes

Reaction equation

HRID 2425364 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 sodium hydrogencarbonate aqueous solution were added thereto, and the resulting solution was extracted with ethyl acetate, washed with saturated sodium hydrogencarbonate aqueous solution and then with saturated 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 sodium hydrogencarbonate aqueous solution
  4. dry with materialwith saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-17d51baad8874d9aa7d7d0be805f6085
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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