HCID 23114101, compound → HCID 52935173, compound

HRID 2376312Notes

Reaction equation

HRID 2376312 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[C:15]([CH3:21])=[C:16]([NH2:20])[C:17]([CH3:19])=[CH:18][C:13]=3[O:12][CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>C(O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[C:14]3[C:15]([CH3:21])=[C:16]([NH2:20])[C:17]([CH3:19])=[CH:18][C:13]=3[O:12][CH2:11]2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 23114101HCID 23114101, compound

Product 1

HCID 52935173HCID 52935173, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 32 (22.5 g, 80 mmol) and (2S, 3S)-(4′-methyl)-tartranilic acid (19.14 g, 80 mmol) in ethanol (480 mL) was heated at 85° C. for dissolution. The solution was cooled to 0° C. for 2 hours, and the precipitated crystals were taken. The crystals were washed with cold ethanol, and then were dried under reduced pressure. The obtained crystals were suspended in a 2 N aqueous sodium hydroxide solution (400 mL), which was extracted with diethyl ether. The extract was washed with a saturated sodium hydrogen carbonate solution and a saturated brine, and then was dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 9.44 g (yield 34%) of the title compound as an oily matter. The obtained oily matter was, if necessary, crystallized with cold hexane. Melting point: 53-55° C. [α]D20=+64.0° (c=0.44, chloroform).

Workup

  1. temperatureThe solution was cooled to 0° C. for 2 hours
  2. washThe crystals were washed with cold ethanol
  3. customwere dried under reduced pressure
  4. extractionwas extracted with diethyl ether
  5. washThe extract was washed with a saturated sodium hydrogen carbonate solution
  6. dry with materiala saturated brine, and then was dried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-54e9e2145e4f4dc09a6751ca7efa2b00
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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