Triethylamine → (+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-(pyrrolidinoformamido)tetraline

HRID 322614

반응식

HRID 322614 반응식
[N:1]1([C:6]([NH2:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.C(N(CC)CC)C.[Cl:21][C:22]1[CH:23]=[C:24]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:25]([NH:27][C@@H:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35](N)[CH:36]=2)[CH2:31][CH2:30][C@H:29]1[O:39][C:40](=[O:42])[CH3:41])=[O:26]>C(Cl)Cl>[Cl:21][C:22]1[CH:23]=[C:24]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:25]([NH:27][C@@H:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([NH:8][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[CH:36]=2)[CH2:31][CH2:30][C@H:29]1[O:39][C:40](=[O:42])[CH3:41])=[O:26]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1383351-PyrrolidinecarboxamideHCID 12042344(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-aminotetraline

생성물 1

HCID 21338527(+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-(pyrrolidinoformamido)tetraline

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of pyrrolidine carboxamide (1.5 mL) in CH2Cl2 (25 mL) was treated with POCl3 (0.23 mL). After 1.5 h, the solution was treated with triethylamine (1 mL) and 115 (0.5 g). After stirring over night, the solvent was evaporated, the residue was treated with ice-water, the mixture neutralized, and the mixture extracted with EtOAc. The extracts were washed with brine and the solvent was dried and evaporated to give a dark oil. The oil was purified by radial chromatography eluting with 5% EtOH-CHCl3 to give a tan solid that was recrystallized from EtOAc to give a white solid (0.18 g), m.p. 229° C., dec.

후처리

  1. customthe solvent was evaporated
  2. additionthe residue was treated with ice-water
  3. extractionthe mixture extracted with EtOAc
  4. washThe extracts were washed with brine
  5. customthe solvent was dried
  6. customevaporated
  7. customto give a dark oil
  8. customThe oil was purified by radial chromatography
  9. washeluting with 5% EtOH-CHCl3
  10. customto give a tan solid
  11. customthat was recrystallized from EtOAc

출처 및 근거

ORD 기록
ord-731b390b35574151a24e1a043bfda210
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211364B1

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