Citric Acid → HCID 58306597, compound

HRID 1909854Notes

Reaction equation

HRID 1909854 reaction equation
C[N:2]1[C:7]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:6]=2[C:5](=[O:15])O[C:3]1=O.C(O)C.Cl.[NH2:21][C@H:22]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)[CH3:23].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C.C(N(CC)CC)C>[CH3:3][NH:2][C:7]1[S:8][C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:6]=1[C:5]([NH:21][C@H:22]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)[CH3:23])=[O:15]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochlorideHCID 58306551HCID 58306551, compound

Product 1

HCID 58306597HCID 58306597, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-methyl-5,6,7,8-tetrahydro-2H-[1]benzothieno[2,3-d][1,3]oxazine-2,4(1H)-dione (0.50 g) was added ethanol (20 mL), and triethylamine (0.44 mL) and methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride were sequentially added, followed by heating with reflux for 18 hours. The reaction mixture was cooled to room temperature, and a 10% aqueous citric acid solution (15 mL) was added thereto. To a mixture was added ethyl acetate, followed by washing with water, and the obtained organic layer was dried over anhydrous sodium sulfate. After filtering and concentrating under reduced pressure, the residue was purified by silica gel column chromatography (hexane/ethyl acetate: 90/10-75/25) to obtain methyl 4-[(1S)-1-({[2-(methylamino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)ethyl]benzoate (0.42 g).

Workup

  1. additionwere sequentially added
  2. temperatureby heating
  3. temperaturewith reflux for 18 hours
  4. washby washing with water
  5. dry with materialthe obtained organic layer was dried over anhydrous sodium sulfate
  6. filtrationAfter filtering
  7. concentrationconcentrating under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate: 90/10-75/25)

Sources & evidence

ORD record
ord-e3dee8e034614f839be8dfac0cebfe86
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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