Dicyclohexylcarbodiimide → Fmoc-asn(trt)-opfp

HRID 1110196

반응식

HRID 1110196 반응식
[NH:1]([C:29]([O:31][CH2:32][CH:33]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30])[C@H:2]([C:26]([OH:28])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:46][C:47]1[C:52](O)=[C:51]([F:54])[C:50]([F:55])=[C:49]([F:56])[C:48]=1[F:57].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[NH:1]([C:29]([O:31][CH2:32][CH:33]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30])[C@H:2]([C:26]([O:28][C:52]1[C:47]([F:46])=[C:48]([F:57])[C:49]([F:56])=[C:50]([F:55])[C:51]=1[F:54])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 640248Fmoc-Asn(Trt)-OH

생성물 1

HCID 15138257Fmoc-asn(trt)-opfp

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1.5 g (2.51 mmol) of Fmoc-Asn(Trt)-OH are dissolved in 15 ml of tetrahydrofuran. 0.51 g (2.76 mmol) of pentafluoro-phenol is added, the solution is cooled to 0° and then 0.57 g (2.76 mmol) of dicyclohexyl-carbodiimide is also added in solid form. It is stirred at 0° for 30 minutes, at room temperature for 2 hours and again at 0° for 30 minutes. The dicyclohexylurea which has crystallized out is filtered off, and the filtrate is evaporated to dryness and triturated with 40 ml of diisopropyl ether. The powdery residue is filtered off, dried and recrystallized from methylene chloride/petroleum ether. Fmoc-Asn(Trt)-OPfp is obtained; m.p. 154°-156°, [α]D20 =-7.8° (THF).

후처리

  1. temperaturethe solution is cooled to 0°
  2. customThe dicyclohexylurea which has crystallized out
  3. filtrationis filtered off
  4. customthe filtrate is evaporated to dryness
  5. customtriturated with 40 ml of diisopropyl ether
  6. filtrationThe powdery residue is filtered off
  7. customdried
  8. customrecrystallized from methylene chloride/petroleum ether

출처 및 근거

ORD 기록
ord-81158b16d707489b8214ac7ac824e4a5
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324833

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