Acetyl chloride → HCID 59683512, compound

HRID 2389643Notes

Reaction equation

HRID 2389643 reaction equation
C(Cl)(=O)C.C(O[C:10]([N:12](C)[CH:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH2:34][C:35]2[CH:36]=[C:37]([C:43]3[CH:48]=[CH:47][N:46]=[C:45]([C:49]([O:51][CH3:52])=[O:50])[CH:44]=3)[CH:38]=[CH:39][C:40]=2[O:41][CH3:42])[C:20]([C:22]2[S:26][C:25]3[C:27]([F:32])=[CH:28][CH:29]=[C:30]([F:31])[C:24]=3[C:23]=2[Cl:33])=[O:21])[CH2:15][CH2:14]1)=O)(C)(C)C>CO>[Cl:33][C:23]1[C:24]2[C:30]([F:31])=[CH:29][CH:28]=[C:27]([F:32])[C:25]=2[S:26][C:22]=1[C:20]([N:19]([CH2:34][C:35]1[CH:36]=[C:37]([C:43]2[CH:48]=[CH:47][N:46]=[C:45]([C:49]([O:51][CH3:52])=[O:50])[CH:44]=2)[CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[CH:16]1[CH2:17][CH2:18][CH:13]([NH:12][CH3:10])[CH2:14][CH2:15]1)=[O:21]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 59683538HCID 59683538, compound

Product 1

HCID 59683512HCID 59683512, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (5 mL) is added to anhydrous MeOH (10 mL) at 0° C. tert-Butyl carbamate 148 (247 mg, 0.35 mmol) is then treated with this solution and stirred 2 h. On removal of the solvents in vacuo, the reaction mixture is dissolved in DCM (25 mL) and extracted into 2 M HCl (4×10 mL). The combined HCl phases are washed with DCM (2×20 mL) then taken to pH 9 by careful addition of solid NaHCO3. The resultant aqueous suspension is then extracted into DCM (3×20 mL), the combined DCM phases dried (Na2SO4) and reduced in vacuo to afford the title compound.

Workup

  1. additionis then treated with this solution
  2. customOn removal of the solvents in vacuo
  3. dissolutionthe reaction mixture is dissolved in DCM (25 mL)
  4. extractionextracted into 2 M HCl (4×10 mL)
  5. washThe combined HCl phases are washed with DCM (2×20 mL)
  6. additionthen taken to pH 9 by careful addition of solid NaHCO3
  7. extractionThe resultant aqueous suspension is then extracted into DCM (3×20 mL)
  8. dry with materialthe combined DCM phases dried (Na2SO4)

Sources & evidence

ORD record
ord-894191bdacba431ca6a278f5a0756293
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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