Benzyl chloroformate → HCID 86725344, compound

HRID 925237Notes

Reaction equation

HRID 925237 reaction equation
[F:1][C:2]1([F:17])[C:10](=[O:11])[C:9]2[C:8]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:7]=3[CH:6]=[CH:5][C:4]=2[CH2:3]1.CCN(C(C)C)C(C)C.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>C(Cl)Cl.Cl>[CH2:31]([O:30][C:28]([N:14]1[CH2:15][CH2:16][C:7]2=[CH:6][CH:5]=[C:4]3[C:9]([C:10](=[O:11])[C:2]([F:1])([F:17])[CH2:3]3)=[C:8]2[CH2:12][CH2:13]1)=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 86725323HCID 86725323, compound

Product 1

HCID 86725344HCID 86725344, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from step (a) (0.13 g, 0.56 mmol) dissolved in DCM (5 ml) at 0° C. was added DIEA (0.12 ml, 0.67 mmol) and benzyl chloroformate (0.095 ml, 0.67 mmol). The reaction mixture was allowed to stir at RT for 1 hour. The reaction mixture was diluted with 1N HCl and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried (Na2SO4), and solvent evaporated in vacuo to give the crude product which was purified by flash silica-gel chromatography (gradient elution: 0-40% EtOAc in hexanes) to give the sub-title compound as a colorless oil (180 mg). MS: ESI (positive): 372 (M+H).

Workup

  1. extractionextracted with DCM (3×)
  2. washThe combined DCM extracts were washed with brine
  3. dry with materialdried (Na2SO4), and solvent
  4. customevaporated in vacuo
  5. customto give the crude product which
  6. customwas purified by flash silica-gel chromatography (gradient elution: 0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c3a378048f7f4507913fae46c69c0427
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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