Hydrogen chloride-ethyl acetate → HCID 57978651, compound

HRID 1866858Notes

Reaction equation

HRID 1866858 reaction equation
Cl.CCOC(C)=O.C(OC([NH:15][NH:16][C:17](=[O:49])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)=[CH:20][C:19]=1[C:36]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:41][CH:40]2[CH2:42][CH:37]1[CH2:38][CH2:39]2)=O)(C)(C)C>C(Cl)Cl>[C:43]1([C:36]2([C:19]3[CH:20]=[C:21]([O:24][CH2:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[CH:22]=[CH:23][C:18]=3[C:17]([NH:16][NH2:15])=[O:49])[CH2:41][CH:40]3[CH2:42][CH:37]2[CH2:38][CH2:39]3)[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57978675HCID 57978675, compound

Product 1

HCID 57978651HCID 57978651, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cold hydrogen chloride/EtOAc (10 mL; saturated solution) was added to a stirred solution of 4c (0.99 g, 1.76 mmol) in methylene chloride (5 mL) at room temperature. After approximately 1 h, the reaction mixture was concentrated in vacuo and the crude residue partitioned between saturated aqueous sodium bicarbonate and methylene chloride. The organic phase was separated, and the aqueous phase was re-extracted twice with methylene chloride. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to afford 4d as a white powder (m/z (ES) 464 (MH)+) which was used without further purification in the subsequent reaction.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe crude residue partitioned between saturated aqueous sodium bicarbonate and methylene chloride
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was re-extracted twice with methylene chloride
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39cfe2c4fdea47a6835bd0ba05e61229
Source dataset
uspto-grants-2009_12
Patent number
US07629467B2

Reaction notes

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