Acetic Anhydride → (R)-tert-butyl 4-(7-acetoxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate

HRID 75399노트

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HRID 75399 반응식
[CH3:1][C:2]([O:4][C:5]([CH3:7])=[O:6])=O.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[CH:25][N+:24]([O-])=[C:23]3C[CH2:29][C@@H:30](C)[C:22]=23)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>>[C:5]([O:4][CH:2]1[C:23]2[N:24]=[CH:25][N:26]=[C:21]([N:18]3[CH2:19][CH2:20][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:16][CH2:17]3)[C:22]=2[C@H:30]([CH3:29])[CH2:1]1)(=[O:6])[CH3:7]

참가 물질

3

반응물 2

HCID 7918Acetic AnhydrideHCID 67338667(R)-4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide

생성물 1

HCID 59580360(R)-tert-butyl 4-(7-acetoxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate수율 100%

반응 조건

온도
90 °C

실험 절차

Ac2O (77.0 mL, 816 mmol) was added to (R)-4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide (21.0 g, 62.8 mmol). The reaction mixture was heated under nitrogen in a 90° C. sand bath and stirred for 100 minutes. The reaction mixture was cooled to room temperature, and excess acetic anhydride was removed by rotary evaporation. The resulting oil was dissolved in DCM, which was then poured carefully into ice saturated Na2CO3. The mixture was extracted with DCM, and the combined extracts were dried (Na2SO4), filtered and concentrated to give (5R)-tert-butyl 4-(7-acetoxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (23.6 g, 100%) as a foam. LC/MS (APCI+) m/z 377.1 [M+H]+.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customexcess acetic anhydride was removed by rotary evaporation
  3. dissolutionThe resulting oil was dissolved in DCM
  4. additionwhich was then poured carefully into ice saturated Na2CO3
  5. extractionThe mixture was extracted with DCM
  6. dry with materialthe combined extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c3f30c1b909a42d39923a72f673ca86e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835434B2

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