Hydrochloric Acid → HCID 66648536, compound

HRID 1774413Notes

Reaction equation

HRID 1774413 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:31]=[CH:30][C:15]([CH2:16]/[C:17](=[C:22](\[CH:27]([CH3:29])[CH3:28])/[C:23]([O:25][CH3:26])=[O:24])/[C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=1)=O)(C)(C)C.Cl.ClCCl.CO>CO>[CH3:21][O:20][C:18](=[O:19])/[C:17](/[CH2:16][C:15]1[CH:30]=[CH:31][C:12]([O:11][CH2:10][CH2:9][NH2:8])=[CH:13][CH:14]=1)=[C:22](/[CH:27]([CH3:28])[CH3:29])\[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226129Dichloromethane methanolHCID 66648457HCID 66648457, compound

Product 1

HCID 66648536HCID 66648536, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of dimethyl 2-{4-[2-(t-butoxycarbonylamino)ethoxy]benzyl}-3-isopropylmaleate (287 mg, 0.659 mmol) in methanol (6 mL) was added 5 M hydrochloric acid (5.9 mL) at room temperature, and the mixture was left standing at room temperature for 20 h. The residue obtained by concentrating the mixture under reduced pressure was dissolved in ethyl acetate, and a saturated aqueous sodium hydrogen carbonate solution was added. After separating the phases, the organic layer was concentrated and the residue thus obtained was subjected to LH-20 (dichloromethane-methanol 1:1) to give 222 mg of the title compound as oil (quantitative).

Workup

  1. waitthe mixture was left
  2. customThe residue obtained
  3. concentrationby concentrating the mixture under reduced pressure
  4. dissolutionwas dissolved in ethyl acetate
  5. additiona saturated aqueous sodium hydrogen carbonate solution was added
  6. customAfter separating the phases
  7. concentrationthe organic layer was concentrated
  8. customthe residue thus obtained

Sources & evidence

ORD record
ord-64d6ca12d19a4fe093acc019e4b8b873
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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