Methanol → 5-(4-aminobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

HRID 441220노트

반응식

HRID 441220 반응식
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:28])[C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH2:10][CH2:9][C:8]1=[O:29])=[O:5])[CH3:2].CO>[Fe].C(O)(=O)C>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:8](=[O:29])[CH2:9][CH2:10]2)=[O:28])=[CH:20][CH:21]=1

참가 물질

5

반응물 2

HCID 887MethanolHCID 106684941-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

생성물 1

HCID 104992005-(4-aminobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one수율 98.9%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

The mixture of 1-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (667 mg), iron powder (469 mg), methanol (10 ml) and acetic acid (1 ml) was refluxed for 1 hour. The reaction mixture was cooled to ambient temperature and it was filtered through a bed of celite followed by the removal of methanol. The residue was diluted with chloroform and to the mixture was added saturated sodium bicarbonate aqueous solution followed by stirring for 10 minutes. The resulting mixture was filtered through a bed of celite and the organic layer was washed with brine. Drying the filtrate, and the removal of chloroform obtained a crude product. The crude product was triturated with a mixture of diisopropyl ether and n-hexane (1:1) to give 5-(4-aminobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (610 mg) as a slightly brown powder.

후처리

  1. temperaturewas refluxed for 1 hour
  2. filtrationit was filtered through a bed of celite
  3. customfollowed by the removal of methanol
  4. additionThe residue was diluted with chloroform and to the mixture
  5. additionwas added saturated sodium bicarbonate aqueous solution
  6. filtrationThe resulting mixture was filtered through a bed of celite
  7. washthe organic layer was washed with brine
  8. customDrying the filtrate
  9. customthe removal of chloroform
  10. customobtained a crude product
  11. customThe crude product was triturated with a mixture of diisopropyl ether and n-hexane (1:1)

출처 및 근거

ORD 기록
ord-963f6592c1d4418eb6492f2dc72f6b6e
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521170

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