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Sodium Carbonate → 5-(2-Fluoro-6-[1,2,3]triazol-2-yl-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester

HRID 1524900
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HRID 1524900 반응식
C(=O)([O-])[O-].[Na+].[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:21][CH:20]2[CH:16]([CH2:17][NH:18][CH2:19]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[F:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([N:32]2[N:36]=[CH:35][CH:34]=[N:33]2)[C:24]=1[C:25](Cl)=[O:26]>C1(C)C=CC=CC=1>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH:16]2[CH:20]([CH2:19][N:18]([C:25](=[O:26])[C:24]3[C:28]([N:32]4[N:33]=[CH:34][CH:35]=[N:36]4)=[CH:29][CH:30]=[CH:31][C:23]=3[F:22])[CH2:17]2)[CH2:21]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]
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5

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HCID 10340Sodium Carbonate2회HCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 866691682-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl chloride

생성물 1

HCID 671161965-(2-Fluoro-6-[1,2,3]triazol-2-yl-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester수율 76.8%

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
0 °C

실험 절차

In a 3-neck round bottom 100 mL flask was added toluene (8.5 mL), aqueous sodium carbonate (1.42 g in 10.7 mL water), and Intermediate 15 (0.905 mg, 4.26 mmol). The biphasic mixture was cooled to 0° C. After cooling to 0° C., 2-fluoro-6-[1,2,3]triazol-2-yl-benzoyl chloride was poured over the stirring biphasic mixture of amine and aqueous sodium carbonate. An exotherm was observed. The mixture was allowed to warm to room temperature. After 1 h, a sample of the organic layer was quenched into methanol and a small amount of acid chloride was determined to remain (observed as its methyl ester). Additional amine (˜50 mg) was added and the mixture was stirred overnight at room temperature. At the end of this period, the layers were separated and 100 mL of methanol were added to the organic layer. The organic was concentrated and purified using flash column chromatography (FCC), gradient of 5-50% of a solution of 10% MeOH, 0.1% NH4OH in DCM/DCM. The desired fractions were combined and concentrated to provide a white foamy solid (1.327 g, 76.8%). MS (ESI): mass calculated for C20H24FN5O3, 401.44, m/z found 346.2 [M+H-56]+. 1H NMR (400 MHz, CDCl3): 7.91-7.73 (m, 3H), 7.53-7.39 (m, 1H), 7.18-7.06 (m, 1H), 4.00-2.76 (m, 10H), 1.52-1.33 (m, 9H).

후처리

  1. temperatureAfter cooling to 0° C.
  2. temperatureto warm to room temperature
  3. customa sample of the organic layer was quenched into methanol
  4. additionAdditional amine (˜50 mg) was added
  5. customAt the end of this period, the layers were separated
  6. addition100 mL of methanol were added to the organic layer
  7. concentrationThe organic was concentrated
  8. custompurified
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bc7e770917014473bea54b011c33630d
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079911B2

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