Water → HCID 15278639, compound

HRID 129387Notes

Reaction equation

HRID 129387 reaction equation
[F:1][C:2]1[C:15](N=C(Cl)C)=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[CH3:20][O:21][C:22](=[O:32])[C:23]1[CH2:31][CH2:30][CH2:29][CH2:28][C:24]=1[C:25]([NH2:27])=[O:26].C(N([CH2:38][CH3:39])CC)C.[OH2:40]>C1C=CC=CC=1>[CH3:20][O:21][C:22](=[O:32])[C:23]1[CH2:31][CH2:30][CH2:29][CH2:28][C:24]=1[C:25]([N:27]([C:38](=[O:40])[CH3:39])[C:15]1[C:2]([F:1])=[CH:3][C:4]2[O:9][CH2:8][C:7](=[O:10])[N:6]([CH2:11][C:12]#[CH:13])[C:5]=2[CH:14]=1)=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15278638HCID 15278638, compoundHCID 15334633Methyl 2-carbamoylcyclohex-1-ene-1-carboxylate

Product 1

HCID 15278639HCID 15278639, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

First, 0.44 g of N-(7-fluoro-4-propargyl-2H-1,4-benzoxazine-3(4H)-one-6-yl)-acetimidoylchloride and 0.29 g of 3,4,5,6-tetrahydrophthalamic acid monomethyl ester were dissolved in 15 ml of benzene, and 0.17 g of triethylamine was added to the solution at room temperature. After that the stirring was continued for 2 hr at 60° C. After letting the reaction liquid stand to cool the same, it was poured into cool water, and then the organic layer was separated therefrom. The organic layer was washed first with water and then with saturated brine, and then dried by using anhydrous magnesium sulfate. The solvent was concentrated, and then the residue was treated by silica gel column chromatography (development solvent: ethyl acetate/n-hexane) to obtain N-acetyl-N-(7-fluoro-4-propargyl-2H-1,4-benzoxazine-3(4H)-one-6-yl)-3,4,5,6tetrahydrophthalamic acid methyl ester. The melting point was 153°-154° C.

Workup

  1. customthe reaction liquid stand
  2. temperatureto cool the same, it
  3. additionwas poured
  4. customthe organic layer was separated
  5. washThe organic layer was washed first with water
  6. dry with materialwith saturated brine, and then dried
  7. concentrationThe solvent was concentrated
  8. additionthe residue was treated by silica gel column chromatography (development solvent: ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-a5cfd52a4985444cae2a1db220ee2bdd
Source dataset
uspto-grants-1995_11
Patent number
US05468719

Reaction notes

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