Hydrochloric Acid → HCID 69278721, compound

HRID 1619745Notes

Reaction equation

HRID 1619745 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][CH:15]1[CH2:30][NH:29][CH2:28][CH2:27][C:16]21[O:20][N:19]=[C:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:17]2.Cl>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:29]2[CH2:28][CH2:27][C:16]3([O:20][N:19]=[C:18]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:17]3)[CH:15]([CH3:14])[CH2:30]2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 69278473HCID 69278473, compound

Product 1

HCID 69278721HCID 69278721, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Tert-butylphenyl isocyanate [260 mg, 1.48 mmol, dissolved in abs. THF (1 ml)] was added to a solution of compound U (320 mg crude product, approx. 1.39 mmol) in abs. THF (20 ml) under argon at RT within 10 min. The mixture was stirred for two hours and then mixed with 2N HCl solution (10 ml). The acidic reaction mixture was stirred for 10 min and then extracted with EtOAc (3×20 ml). The combined organic phases were washed with sat. NaHCO3 solution (10 ml), dried over Na2SO4 and concentrated to dryness under vacuum. The residue obtained was purified by flash chromatography (mobile solvent:cyclohexane/EtOAc=7:3). 6-Methyl-3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide was thus obtained as a diastereoisomer mixture (melting point from 65° C.) in a yield of 170 mg (30%).

Workup

  1. stirringThe acidic reaction mixture was stirred for 10 min
  2. extractionextracted with EtOAc (3×20 ml)
  3. washThe combined organic phases were washed with sat. NaHCO3 solution (10 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness under vacuum
  6. customThe residue obtained
  7. customwas purified by flash chromatography (mobile solvent:cyclohexane/EtOAc=7:3)

Sources & evidence

ORD record
ord-9ef7df01b0f442a99e002ab185323324
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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