Ethyl chloroformate → HCID 67279031, compound

HRID 1694430Notes

Reaction equation

HRID 1694430 reaction equation
C(OC([Cl:6])=O)C.[CH2:7]([NH:9][C:10]([CH:12]1[CH2:15][C:14]([F:29])([C:16]2[CH:21]=[CH:20][C:19]([CH2:22]N3CCCC3)=[C:18]([F:28])[CH:17]=2)[CH2:13]1)=[O:11])[CH3:8]>ClCCCl>[CH2:7]([NH:9][C:10]([CH:12]1[CH2:15][C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][Cl:6])=[C:18]([F:28])[CH:17]=2)([F:29])[CH2:13]1)=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 16119086935840-31-6

Product 1

HCID 67279031HCID 67279031, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Ethylchloroformate (0.505 ml, 5.28 mmol) was added to a solution of Example 16, 3-fluoro-3-(3-fluoro-4-pyrrolidin-1-ylmethyl-phenyl)-cyclobutanecarboxylic acid ethylamide (1.7 g, 5.28 mmol) in DCE (50 ml) After 1 hr stirring at rt. the reaction was quenched with saturated aq. NaHCO3 (150 ml) and extracted with CH2Cl2 (3×100 ml) to recover a residual oil. This was purified by flash column chromatography using a 120 g ISCO™ cartridge and 35% and 40% EtOAc/hexanes to obtain an intermediate 3-(4-chloromethyl-3-fluoro-phenyl)-3-fluoro-cyclobutanecarboxylic acid ethylamide (1.1 g, 75% yield).

Workup

  1. customthe reaction was quenched with saturated aq. NaHCO3 (150 ml)
  2. extractionextracted with CH2Cl2 (3×100 ml)
  3. customto recover a residual oil
  4. customThis was purified by flash column chromatography

Sources & evidence

ORD record
ord-b7aeadb383ce4796b31b775c34f03986
Source dataset
uspto-grants-2012_04
Patent number
US08158673B2

Reaction notes

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