Water → HCID 66793895, compound

HRID 2035304Notes

Reaction equation

HRID 2035304 reaction equation
[OH:1][C:2]1[C:6]2([CH2:11][CH2:10][N:9]([O:12][CH3:13])[CH2:8][CH2:7]2)[O:5][C:4](=[O:14])[C:3]=1[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23].C(N(CC)CC)C.Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33].O>C1COCC1>[CH3:13][O:12][N:9]1[CH2:10][CH2:11][C:6]2([O:5][C:4](=[O:14])[C:3]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])=[C:2]2[O:1][C:32](=[O:33])[O:34][CH2:35][CH3:36])[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 59584737HCID 59584737, compound

Product 1

HCID 66793895HCID 66793895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of crude (ca 50% purity) 4-hydroxy-8-methoxy-3-(2,4,6-trimethyl-phenyl)-1-oxa-8-aza-spiro[4.5]dec-3-en-2-one (1.0 g, 3.15 mmol), triethylamine (0.8 ml, 0.57 g, 5.67 mmol) in 6 ml THF at 0° C. under argon was added ethyl chloroformate (0.36 ml, 0.41 g, 3.78 mmol) dropwise. The suspension became immediately quite thick. It was diluted with additional 2 ml THF while stirring was continued at 0° C. for 30 minutes. The reaction mixture was poured into cold water (0° C.) and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated. The crude product (brown oil) was purified by column chromatography on silica gel (ethyl acetate/cyclohexane 1:1). Yield: 220 mg of carbonic acid ethyl ester 8-methoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1-oxa-8-aza-spiro[4.5]dec-3-en-4-yl ester (title compound P1.5) as a white solid.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product (brown oil) was purified by column chromatography on silica gel (ethyl acetate/cyclohexane 1:1)

Sources & evidence

ORD record
ord-271b1a3e8aa74882866453cba53c93df
Source dataset
uspto-grants-2013_11
Patent number
US08574607B2

Reaction notes

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