Diisopropylethylamine → 6-(Tert-butoxycarbonyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylic acid

HRID 1183810노트

반응식

HRID 1183810 반응식
C1C2=C3C(=CC=C2NC1)NC(C(OC)=O)=C3.[C:17]([O:21][C:22]([N:24]1[C:35]2[C:27](=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][C:30]([C:36]([O:38]C)=[O:37])=[CH:29]3)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].CCN(C(C)C)C(C)C>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[C:35]2[C:27](=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][C:30]([C:36]([OH:38])=[O:37])=[CH:29]3)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 151147736-tert-butyl 2-methyl 7,8-dihydropyrrolo[3,2-e]indole-2,6(3H)-dicarboxylateHCID 15480266Methyl 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate

생성물 1

HCID 139953326-(Tert-butoxycarbonyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylic acid수율 215%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

A solution of 4 (16 mg, 0.015 mmol) and 5 (6.2 mg, 0.02 mmol) in DMF (2 mL) was treated with DIPEA (10 uL). The reaction mixture was stirred for 1 hr at 25° C. The final product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column), eluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient: 10% acetonitrile in 5 min, 10% to 50% acetonitrile in 15 min, maintaining 50% acetonitrile in 5 min, 50% to 100% acetonitrile in 5 min, to obtain 6 (13 mg, 75%). MS: calcd for C51H55BrN10O9 (M+H) m/z 1031.33 found 1031.6.

후처리

  1. customThe final product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column)
  2. washeluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient
  3. wait10% acetonitrile in 5 min
  4. wait10% to 50% acetonitrile in 15 min
  5. temperaturemaintaining 50% acetonitrile in 5 min
  6. wait50% to 100% acetonitrile in 5 min

출처 및 근거

ORD 기록
ord-87bc94260e35482589960e4f3b6f30da
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664407B2

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