Water → HCID 178429100, compound

HRID 2078331Notes

Reaction equation

HRID 2078331 reaction equation
BrC1[CH:11]=[C:10]2[C:5]([C:6](=[O:26])[C:7]([C:15]([NH:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[O:16])=[C:8]([OH:14])[C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[C]=O.CC[O:51][C:52]([CH3:54])=[O:53]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]([CH2:18][NH:17][C:15]([C:7]1[C:6](=[O:26])[C:5]2[CH:4]=[CH:3][C:54]([C:52]([OH:51])=[O:53])=[CH:11][C:10]=2[C:9]([CH3:12])([CH3:13])[C:8]=1[OH:14])=[O:16])([OH:21])=[O:20]

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 178418416HCID 178418416, compoundHCID 178451288HCID 178451288, compound

Product 1

HCID 178429100HCID 178429100, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

Tert-butyl 2-(7-bromo-2-hydroxy-1,1-dimethyl-4-oxo-1,4-dihydronaphthalene-3-carboxamido)acetate (253 mg, 596 μmol, Example 53A-E), trans-dichlorobis(triphenylphosphine)palladium (II) (21 mg, 30 μmol), and triphenylphosphine (16 mg, 60 μmol) were added to a vial, followed by water (32 μL, 1789 μmol) and n-tributylamine (1491 μL). The reaction mixture was placed under 4 atm of carbon monoxide at 90° C. for 18 hours. The reaction mixture was diluted with 50 mL of EtOAc, washed 3 times with 50 mL of 5 N NaOH (aqueous), and separated. The aqueous layer was acidified to pH 2 with concentrated HCl and extracted 2 times with 50 mL of EtOAc, dried over sodium sulfate, and concentrated via rotovap to give the title compound. MS (ESI) m/z: Calculated; 333.3: Observed; 334.0.

Workup

  1. washwashed 3 times with 50 mL of 5 N NaOH (aqueous)
  2. customseparated
  3. extractionextracted 2 times with 50 mL of EtOAc
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-04c01de7a69d4886b00150f9739b63a0
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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