4-Methylmorpholine → HCID 22942158, 화합물

HRID 362144

반응식

HRID 362144 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24](O)=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:42][CH:43]([B:46]1[O:50][C:49]([CH2:52][CH2:53][CH:54]([CH3:63])[CH2:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])([CH3:51])[C:48]([CH3:65])([CH3:64])[O:47]1)[CH2:44][CH3:45]>ClCCl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24]([NH:42][CH:43]([B:46]3[O:50][C:49]([CH2:52][CH2:53][CH:54]([CH3:63])[CH2:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])([CH3:51])[C:48]([CH3:64])([CH3:65])[O:47]3)[CH2:44][CH3:45])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 1549133Fmoc-leucineHCID 22619085HCID 22619085, 화합물

생성물 1

HCID 22942158HCID 22942158, 화합물수율 58.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-10 °C

실험 절차

0.5 g (1.42 mmol) of N-[(9-fluorenyl)methoxycarbonyl]-L-leucine was dissolved in 7 ml of dichloromethane. 0.6 ml (5.7 mmol) of N-methylmorpholine was added and the solution was cooled to -10° C.under a nitrogen atmosphere. 0.22 ml (1.7 mmol) of isobutyl chloroformate was added and the solution was stirred for 7 minutes at -10° C. 1 g(2.13 mmol) of tert-butyl 5-[2-(1(RS)-aminopropyl)-4(RS),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvalerate was added and the mixture was stirred at room temperature for 16 hours, then diluted with dichloromethane and extracted with 2M hydrochloric acid. The organic phase was extracted with 2M hydrochloric acid and saturated sodium hydrogen carbonate solution and then dried over anhydrous magnesium sulphate. After evaporation the residue was purified by chromatography on silica gel using ethyl acetate/hexane (1:2) for the elution. There was obtained 0.56 g of tert-butyl 5-[2-[1(RS)-[[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]amino]propyl]-4(RS),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvalerate as an oil; MS: m/e 677 [M+H]+.

후처리

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. extractionextracted with 2M hydrochloric acid
  3. extractionThe organic phase was extracted with 2M hydrochloric acid and saturated sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customAfter evaporation the residue
  6. customwas purified by chromatography on silica gel
  7. washfor the elution

출처 및 근거

ORD 기록
ord-5d6c7882af50462ca0f6c31eab2df330
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866684

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