Triethylamine → HCID 66794085, compound

HRID 2035300Notes

Reaction equation

HRID 2035300 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[C:10](=[O:22])[O:11][C:12]2([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[C:13]=1[OH:14].C(N(CC)CC)C.CN(C)C1C=CN=CC=1.CN(C1C=CN=CC=1)C.Cl[C:49]([O:51][CH2:52][CH3:53])=[O:50]>C1COCC1>[CH2:52]([O:51][C:49](=[O:50])[O:14][C:13]1[C:12]2([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[O:11][C:10](=[O:22])[C:9]=1[C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1])[CH3:53]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 23202903HCID 23202903, compoundHCID 66793910HCID 66793910, compound

Product 1

HCID 66794085HCID 66794085, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(2,5-dimethyl-phenyl)-4-hydroxy-8-methoxy-1-oxa-8-aza-spiro[4.5]dec-3-en-2-one (120 mg, 0.40 mmol), triethylamine (0.08 ml, 60 mg, 0.60 mmol) and 4-dimethylaminopyridine DMAP (2 mg, 0.02 mmol) in 4 ml THF at 0° C. was added a solution of ethyl chloroformate (0.05 ml, 52 mg, 0.50 mmol) dissolved in 1 ml THF dropwise. The suspension was kept at 0° C. for 30 minutes under argon and left stirring at room temperature overnight. Then the solvent was removed under vacuum. Ethyl acetate was added to the residue and the precipitation was filtered off. The filtrate was concentrated under vacuum to give the crude product, which was purified by column chromatography on silica gel (ethyl acetate/cyclohexane 1:9). Yield: 111 mg of carbonic acid 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-oxa-8-aza-spiro[4.5]dec-3-en-4-yl ester ethyl ester (title compound P1.1) as a light yellow gum.

Workup

  1. waitleft
  2. customThen the solvent was removed under vacuum
  3. additionEthyl acetate was added to the residue
  4. customthe precipitation
  5. filtrationwas filtered off
  6. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3541bd93972f4eefa02fa55c25f39f27
Source dataset
uspto-grants-2013_11
Patent number
US08574607B2

Reaction notes

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