Methyl chloroformate → HCID 15614944, compound

HRID 620353Notes

Reaction equation

HRID 620353 reaction equation
[H-].[K+].[Cl:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:17])([F:16])[F:15])[C:5]=1[C:20]([NH:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21].Cl[C:32]([O:34][CH3:35])=[O:33]>O1CCCC1>[Cl:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:17])([F:16])[F:15])[C:5]=1[C:20]([N:22]([C:32]([O:34][CH3:35])=[O:33])[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 82127Potassium hydrideHCID 15614966HCID 15614966, compound

Product 1

HCID 15614944HCID 15614944, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of potassium hydride (0.9 g, 1.2 eq, 35% by weight dispersion in mineral oil) in dry tetrahydrofuran (20 mL) under argon at room temperature was added dropwise a solution of N-[[2-chloro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]glycine, 1,1-dimethylethyl ester (2.73 g, 6.53 mmol) in dry THF (30 mL). After stirring 25 minutes the reaction was cooled in an ice bath and a solution of methyl chloroformate (0.7 mL, 1.4 eq) in dry THF (18 mL) was added dropwise over a period of 20 minutes. After stirring 1 hour the reaction was quenched with saturated aqueous ammonium chloride and diluted with ether (300 mL). The ether layer was separated, and dried over magnesium sulfate. Silica gel was added and the ether was removed. The silica absorbate was flash chromatographed (4:1 petroleum ether:EtOAc) to give the title compound as a white solid (2.10 g, 67%). A small sample was further purified by trituration with petroleum ether, m.p. 117°-118° C.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringAfter stirring 1 hour the reaction
  3. customwas quenched with saturated aqueous ammonium chloride
  4. additiondiluted with ether (300 mL)
  5. customThe ether layer was separated
  6. dry with materialdried over magnesium sulfate
  7. additionSilica gel was added
  8. customthe ether was removed
  9. customchromatographed (4:1 petroleum ether:EtOAc)

Sources & evidence

ORD record
ord-c53c3ca870774699ae74c96b6fb99ae8
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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