Water → HCID 178497942, compound

HRID 2213540Notes

Reaction equation

HRID 2213540 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:27])[CH2:12][C:13](=[O:26])[CH2:14][O:15][C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)[CH:5]=1.O.[N:30]([O-])=[O:31].[Na+]>C(O)(=O)C.C1COCC1>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:27])[C:12](=[N:30][OH:31])[C:13](=[O:26])[CH2:14][O:15][C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 86760244HCID 86760244, compound

Product 1

HCID 178497942HCID 178497942, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 3-[4-(adamantan-1-yloxy)-3-oxo-butyrylamino]-benzoic acid methyl ester (9.95 g, 25.8 mmol) in acetic acid (100 mL) and THF (90 mL) was added water (12 mL). The mixture was cooled to 5° C. and an aqueous solution (16 mL) of sodium nitrite (2.31 g, 35.0 mmol) was added dropwise while maintaining the temperature below 10° C. Upon completion of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate. The aqueous phase was discarded and the organic phase was washed with further saturated aqueous NaHCO3 and brine. The organic phase was dried (MgSO4) and the solvent was evaporated at reduced pressure to afford the title product as a yellow foam (10.15 g, 95%). 1H NMR (CDCl3) 11.06 (1H, br s), 8.25 (1H, s), 7.93-7.90 (1H, m), 7.84-7.81 (1H, m), 7.51-7.41 (1H, m), 4.83 (2H, s), 3.95 (3H, s), 2.20 (3H, s), 1.82-1.57 (12H, m).

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. additionUpon completion of the addition
  3. temperatureto warm to room temperature
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate
  6. washthe organic phase was washed with further saturated aqueous NaHCO3 and brine
  7. dry with materialThe organic phase was dried (MgSO4)
  8. customthe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-a17bd0393421499ba24716f0eef276a2
Source dataset
uspto-grants-2006_09
Patent number
US07105558B2

Reaction notes

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