Methyl chloroformate → HCID 58428014, compound

HRID 1473777Notes

Reaction equation

HRID 1473777 reaction equation
[OH:1][N:2]1[C:6]2([CH2:11][CH2:10][N:9]([O:12][CH3:13])[CH2:8][CH2:7]2)[C:5]([O:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])=[C:4]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[C:3]1=[O:29].C(N(CC)CC)C.Cl[C:38]([O:40][CH3:41])=[O:39]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:13][O:12][N:9]1[CH2:10][CH2:11][C:6]2([N:2]([O:1][C:38]([O:40][CH3:41])=[O:39])[C:3](=[O:29])[C:4]([C:20]3[C:21]([CH3:28])=[CH:22][C:23]([CH3:27])=[CH:24][C:25]=3[CH3:26])=[C:5]2[O:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 58427991HCID 58427991, compound

Product 1

HCID 58428014HCID 58428014, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of carbonic acid ethyl ester 1-hydroxy-8-methoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester (preparation example 13, step 1; compound P1ii.11) (140 mg, 0.33 mmol), triethylamine (93 μl, 68 mg, 0.67 mmol) and 4-dimethylaminopyridine (2 mg) in tetrahydrofuran (3 ml) at 0° C. was added a solution of methyl chloroformate (33 μl, 41 mg, 0.43 mmol) in tetrahydrofuran (2 ml) dropwise. The suspension was stirred at 0° C. for one hour, and at room temperature for one hour. The reaction mixture was evaporated, diluted with ethyl acetate and filtered to remove salts. The filtrate was washed with a saturated aqueous sodium hydrogen carbonate solution (2×15 ml) and brine, dried over sodium sulfate and concentrated. The oily residue was purified by chromatography on silica gel (ethyl acetate/hexane 1:2). Yield: 30 mg of carbonic acid ethyl ester 8-methoxy-1-methoxycarbonyloxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester (title compound P1ii.13) as a colorless gum.

Workup

  1. waitat room temperature for one hour
  2. customThe reaction mixture was evaporated
  3. additiondiluted with ethyl acetate
  4. filtrationfiltered
  5. customto remove salts
  6. washThe filtrate was washed with a saturated aqueous sodium hydrogen carbonate solution (2×15 ml) and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe oily residue was purified by chromatography on silica gel (ethyl acetate/hexane 1:2)

Sources & evidence

ORD record
ord-54d35eb1c2504338b4ce70b731f886d4
Source dataset
uspto-grants-2015_04
Patent number
US09018135B2

Reaction notes

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