Methyl chloroformate → HCID 13575671, compound

HRID 279893Notes

Reaction equation

HRID 279893 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[C:7]([CH3:13])=[CH:8][CH:9]=[C:10]([NH:11][NH2:12])[C:4]=2[O:3]1.C(N(CC)C(C)C)(C)C.Cl[C:24]([O:26][CH3:27])=[O:25]>C1COCC1>[CH3:27][O:26][C:24]([NH:12][NH:11][C:10]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:6][C:5]=2[C:7]([CH3:13])=[CH:8][CH:9]=1)=[O:25]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 13575670HCID 13575670, compound

Product 1

HCID 13575671HCID 13575671, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

15.6 g of 1E was mixed with 150 ml of THF and 11.3 g of N,N-diisopropylethylamine. The mixture was cooled to -5° C. and 9.1 g of methyl chloroformate was added drop-by-drop to the stirred mixture, which then was stirred at 0° C. for two hours. The mixture then was poured over ice water and extracted with ether. The extract was dried (MgSO4), filtered and the solvent was evaporated. The residue was column chromatographed on silica gel, using a 1:4:20 v:v:v mixture of tetrahydrofuran, ethyl acetate and hexane as eluent, to give 1, as a tan solid, m.p.: 90°-92° C.

Workup

  1. extractionextracted with ether
  2. dry with materialThe extract was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customchromatographed on silica gel
  6. additionv:v mixture of tetrahydrofuran, ethyl acetate and hexane as eluent
  7. customto give 1

Sources & evidence

ORD record
ord-46f11af2066547cca630656bb0e49279
Source dataset
uspto-grants-1986_05
Patent number
US04587259

Reaction notes

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