Dichloromethane → HCID 69279870, compound

HRID 1619746Notes

Reaction equation

HRID 1619746 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].C(Cl)Cl.[CH2:17]([C:24]1[CH2:28][C:27]2([CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[O:26][N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:31]2[CH2:32][CH2:33][C:27]3([O:26][N:25]=[C:24]([CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:28]3)[CH2:29][CH2:30]2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 59830365HCID 59830365, compound

Product 1

HCID 69279870HCID 69279870, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Tert-butylphenyl isocyanate (0.218 ml, 1.24 mmol), dissolved in abs. DCM (5 ml), was added dropwise to a solution of compound Y (286 mg, 1.24 mmol) in abs. DCM (10 ml) at RT within 20 min. After stirring for 3.5 h at RT, the solution was washed with 10% citric acid solution (1×10 ml) and water (1×10 ml), dried and concentrated. The colourless oil obtained (742 mg) contained few impurities. The oil was mixed with diethyl ether (10 ml) and stored at 5° C. The precipitated solid was removed by suction-filtration and washed with diethyl ether (5 ml). The desired product 3-benzyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide was obtained in a yield of 73% (369 mg) having a melting point of 137-139° C.

Workup

  1. washthe solution was washed with 10% citric acid solution (1×10 ml) and water (1×10 ml)
  2. customdried
  3. concentrationconcentrated
  4. customThe colourless oil obtained (742 mg)
  5. customstored at 5° C
  6. customThe precipitated solid was removed by suction-filtration
  7. washwashed with diethyl ether (5 ml)

Sources & evidence

ORD record
ord-af571469c51e4888b7922af0b51e70c0
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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