N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine → HCID 178454255, 화합물

HRID 1855562노트

반응식

HRID 1855562 반응식
OC(C(F)(F)F)=O.[NH2:8][CH2:9][CH2:10][C:11]1[O:15][C:14]([C@@H:16]2[CH2:22][CH2:21][C@@H:20]3[CH2:23][N:17]2[C:18](=[O:32])[N:19]3[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:13][N:12]=1.[C:33]([O:37][C:38]([NH:40][C:41](=[N:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])N1C=CC=N1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>CO>[C:50]([O:49][C:48]([N:47]=[C:41]([NH:40][C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:39])[NH:8][CH2:9][CH2:10][C:11]1[O:15][C:14]([C@@H:16]2[CH2:22][CH2:21][C@@H:20]3[CH2:23][N:17]2[C:18](=[O:32])[N:19]3[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:13][N:12]=1)=[O:54])([CH3:53])([CH3:52])[CH3:51]

참가 물질

4

반응물 2

HCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 131732349HCID 131732349, 화합물

생성물 1

HCID 178454255HCID 178454255, 화합물수율 70%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

TEA (77 mg, 0.764 mmol) was added to a 0° C. solution of (2S,5R)-2-(5-(2-aminoethyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one TFA salt from the previous step in MeOH (3.0 mL). Tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate (65 mg, 0.209 mmol) was then added at 0° C. and the reaction mixture was stirred at 0° C. for 4 hrs. The reaction mixture was evaporated and the residue was purified by silica gel column chromatography (gradient elution 30%-50% EtOAc/petroleum ether) to give (2S,5R)-2-(5-((2,3-bis(tert-butoxycarbonyl)guanidino)ethyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (80 mg, 70% in 2 steps) as a colorless oil. ESI-MS (EI+, m/z): 586.3 [M+H]+.

후처리

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by silica gel column chromatography (gradient elution 30%-50% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-ec0e6074bc0d45b0b7250c405cadfaca
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962844B2

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