Methyl chloroformate → HCID 59676082, compound

HRID 642769Notes

Reaction equation

HRID 642769 reaction equation
[CH:1]1[C:6]2[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH2:16][S:17][C:5]=2[CH:4]=[C:3](O)[CH:2]=1)=[CH:13][C:12](O)=[CH:11][CH:10]=4.[Li][CH2:21]CCC.Cl[C:26]([O:28][CH3:29])=[O:27]>C1COCC1>[CH3:29][O:28][C:26]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:21])[C:7]1[C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[S:17][CH2:16][C:15]2=1)=[O:27]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 59676065HCID 59676065, compoundHCID 178418339Butyllithium

Product 1

HCID 59676082HCID 59676082, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6,11-dihydro-5-thia-11-aza-benzo[a]fluorene-3,8-diol (1 mmol, 330 mg), as prepared in Example 31, in THF (15 ml) was treated with n-BuLi (2.0 M, 0.6 ml, 1.2 mmol) at −78° C. for 30 minutes, then methyl chloroformate (1 equivalent) was added drop by drop to the reaction mixture at −78° C. After slowly warming up to room temperature, the reaction mixture was quenched by saturated ammonium chloride, extracted by ethyl acetate and purified by chromatography (Hexane:ethyl acetate=5:1) to yield the title compound as a white solid.

Workup

  1. customthe reaction mixture was quenched by saturated ammonium chloride
  2. extractionextracted by ethyl acetate
  3. custompurified by chromatography (Hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-7747e99ab4184a72bde4058440ad92e0
Source dataset
uspto-grants-2010_04
Patent number
US07696239B2

Reaction notes

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