2,2,2-Trichloroethyl chloroformate → HCID 86687043, compound

HRID 630767Notes

Reaction equation

HRID 630767 reaction equation
[C:1]([C:5]1[NH:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[C:8]([NH2:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20]>CCOC(C)=O.[OH-].[Na+].C1CCCCC1>[Cl:24][C:23]([Cl:26])([Cl:25])[CH2:22][O:21][C:19](=[O:20])[NH:10][C:8]1[N:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[NH:6][C:7]=1[C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 86687042HCID 86687042, compound

Product 1

HCID 86687043HCID 86687043, compound

Reagents, catalysts & solvents 3

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of Intermediate 51c (45.3 mg, 0.197 mmol) in EtOAc (1 mL) and aqueous NaOH (1 M, 0.49 mL) was added 2,2,2-trichloroethyl chloroformate (0.0326 mL, 0.237 mmol) and the resulting mixture stirred at RT for 45 min. The layers were separated and the aqueous extracted with EtOAc (2 mL). The combined organics were washed with brine (2 mL), dried (Na2SO4), filtered and concentrated in vacuo to leave an orange-red gum. FCC, using 0-50% EtOAc in cyclohexane, gave the title compound as a pale orange film (44.1 mg, 55%). LCMS (Method 3): Rt 2.87 min, m/z 404, 406 [MH+].

Workup

  1. customThe layers were separated
  2. extractionthe aqueous extracted with EtOAc (2 mL)
  3. washThe combined organics were washed with brine (2 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto leave an orange-red gum

Sources & evidence

ORD record
ord-5bc7d1e3c0b7471c8f8725f74a3df5ef
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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