Triethylamine → Fmoc-Asn(Trt)-OH

HRID 1110189

반응식

HRID 1110189 반응식
C1C(=O)N([O:8][C:9]([O:11][CH2:12][CH:13]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)=O)C(=O)C1.C(N(CC)CC)C.[NH2:33][C@H:34]([C:58]([OH:60])=[O:59])[CH2:35][C:36](=[O:57])[NH:37][C:38]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.S(=O)(=O)(O)[O-].[K+]>O1CCCC1.O.C(OCC)(=O)C>[NH:33]([C:9]([O:11][CH2:12][CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]2[C:25]1=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:8])[C@H:34]([C:58]([OH:60])=[O:59])[CH2:35][C:36](=[O:57])[NH:37][C:38]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

참가 물질

8

반응물 4

HCID 8471Triethylamine2회HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516920Potassium bisulfateHCID 7408309N-(Triphenylmethyl)-L-asparagine

생성물 1

HCID 640248Fmoc-Asn(Trt)-OH

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

3.4 g of 9-fluorenylmethyl N-succinimidyl carbonate (10 mmol) are added and, at the same time, 1.4 ml of triethylamine are added dropwise so that the pH is 8.3-8.7 to a vigorously stirred solution of 3.8 g of H-Asn(Trt)-OH.0.5 H2O (10 mmol) in 20 ml of tetrahydrofuran, 10 ml of water and 1.4 ml of triethylamine (10 mmol). After 20 minutes, the mixture is cooled in an ice bath and ethyl acetate and 25 ml of a one-molar aqueous potassium bisulfate solution are added. The organic phase is washed with water until free of sulfate, dried over sodium sulfate and concentrated under reduced pressure to about 50 g. The Fmoc-Asn(Trt)-OH can be crystallized by slow addition of diisopropyl ether, m.p. 210°-211° (with decomposition).

후처리

  1. temperaturethe mixture is cooled in an ice bath
  2. washThe organic phase is washed with water until free of sulfate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure to about 50 g
  5. customThe Fmoc-Asn(Trt)-OH can be crystallized by slow addition of diisopropyl ether, m.p. 210°-211° (with decomposition)

출처 및 근거

ORD 기록
ord-6029d284f51645518896ddc67f84ada4
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324833

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