Methyl chloroformate → HCID 22912929, compound

HRID 1899965Notes

Reaction equation

HRID 1899965 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][NH:5]2.C(N(C(C)C)CC)(C)C.[CH2:22]1COCC1.Cl[C:28]([O:30][CH3:31])=[O:29]>O>[CH3:22][N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[CH:11][CH:10]=2)[N:5]([C:28]([O:30][CH3:31])=[O:29])[CH2:6][C:7]1=[O:12]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 101035036-fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 22912929HCID 22912929, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.97 g of 6-fluoro-1,2,3,4-tetrahydroquinoxalin-2-one (EXAMPLE 6), 3.1 ml of diisopropylethylamine, and 11 ml of THF is added 1.4 ml of methyl chloroformate. The reaction is cooled with cool tap water as an exotherm ensued. After 35 min, the mixture is partitioned between ethyl acetate, aq. sodium bicarbonate, and saline. The organic layers are dried over magnesium sulfate, concentrated, and the crude product is crystallized from dichloromethane/methanol/ethyl acetate to give 2.06 g of methyl 6-fluoro-1,2,3,4-tetrahydro-4-(methoxycarbonyl)quinoxaline-2-one; mp 206.5°-207.5°; NMR (CDCl3) 3.86, 4.43, 6.84, 7.48, 8.67 δ.

Workup

  1. temperatureThe reaction is cooled
  2. customthe mixture is partitioned between ethyl acetate, aq. sodium bicarbonate, and saline
  3. dry with materialThe organic layers are dried over magnesium sulfate
  4. concentrationconcentrated
  5. customthe crude product is crystallized from dichloromethane/methanol/ethyl acetate

Sources & evidence

ORD record
ord-92022b9411a947cc920e8751175a937b
Source dataset
uspto-grants-1996_11
Patent number
US05574038

Reaction notes

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