Ethyl Acetate → HCID 15200028, compound

HRID 263815Notes

Reaction equation

HRID 263815 reaction equation
B(Br)(Br)Br.[C:5]([NH:13][C@@:14]1([C:26]([O:28]C)=[O:27])[CH2:23][CH2:22][C:21]2[C:16](=[C:17]([O:24]C)[CH:18]=[CH:19][CH:20]=2)[CH2:15]1)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl-].[NH4+].C(OCC)(=O)C>ClCCl>[C:5]([NH:13][C@@:14]1([C:26]([OH:28])=[O:27])[CH2:23][CH2:22][C:21]2[C:16](=[C:17]([OH:24])[CH:18]=[CH:19][CH:20]=2)[CH2:15]1)(=[O:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 86751020HCID 86751020, compound

Product 1

HCID 15200028HCID 15200028, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

28.7 ml of boron tribromide solution (1M in dichloromethane) were added dropwise under argon and while cooling with ice to a solution of 1.95 g (5.75 mmol) of methyl (S)-2-benzamido-8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylate in 15 ml of dichloromethane. The reaction mixture was stirred at 0° for 30 minutes and at room temperature for 3 hours and then poured into a mixture of ice, saturated ammonium chloride solution and ethyl acetate. The organic phase was separated, extracted with saturated sodium chloride solution, dried over MgSO4 and concentrated. The residue was dried in a high vacuum, suspended in diethyl ether/hexane (1:4) and filtered off. The filter residue was dried, there being obtained 1.75 g (97.8%) of (S)-2-benzamido-8-hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid. [α]D =+84.3° (c=0.3, methanol). IR (KBr): 3362m(br.), 3064w, 3022w, 2976w, 2938w, 2620w, 1718s, 1644s, 1588m, 1523s, 1487m, 1467s, 1330m, 1278s, 1082w, 716m.

Workup

  1. customThe organic phase was separated
  2. extractionextracted with saturated sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was dried in a high vacuum
  6. filtrationfiltered off
  7. customThe filter residue was dried

Sources & evidence

ORD record
ord-137bb3f13cb54ab7bc4c211c92ee4623
Source dataset
uspto-grants-1997_07
Patent number
US05644024

Reaction notes

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