Triethylamine → Fmoc-Asn(Trt)-OH

HRID 1110189

反応式

HRID 1110189 の反応式
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

参加物

8

反応物 4

HCID 8471Triethylamine2 回HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516920Potassium bisulfateHCID 7408309N-(Triphenylmethyl)-L-asparagine

生成物 1

HCID 640248Fmoc-Asn(Trt)-OH

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6029d284f51645518896ddc67f84ada4
出典データセット
uspto-grants-1994_06
特許番号
US05324833

関連ノート

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