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4-Methylmorpholine → N-[N-Phthalimido-3-(2-thienyl)-L-alanyl]-6-hydroxy-L-norleucine, methy ester

HRID 1683343
ノート
印刷プレビュー

反応式

HRID 1683343 の反応式
CN1CCOCC1.Cl.[OH:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]([C:16]([O:18][CH3:19])=[O:17])[NH2:15].[C:20]1(=[O:41])[N:24]([NH:25][C@H:26]([C:33](O)=[O:34])[CH2:27][C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)[C:23](=[O:36])[C:22]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:21]12.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C=O>[C:23]1(=[O:36])[N:24]([NH:25][C@H:26]([C:33]([NH:15][C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][OH:9])=[O:34])[CH2:27][C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)[C:20](=[O:41])[C:21]2=[CH:40][CH:39]=[CH:38][CH:37]=[C:22]12
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11680005methyl (2S)-2-amino-6-hydroxyhexanoate hydrochlorideHCID 70051103HCID 70051103、化合物HCID 178418300HCID 178418300、化合物

生成物 1

HCID 131719431N-[N-Phthalimido-3-(2-thienyl)-L-alanyl]-6-hydroxy-L-norleucine, methy ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

N-Methylmorpholine (1.51 ml., 14.5 mmol.) was added to a solution of 6-hydroxy-L-norleucine, methyl ester, hydrochloride (8.53 mmol.) in methylene chloride (34 ml)/dimethylformamide (9 ml.) at room temperature under argon. The resulting mixture was cooled to 0° C. and N-phthalimido-3-(2-thienyl)-L-alanine (2.57 g., 8.54 mmol.), hydroxybenzotriazole (1.19 g., 8.80 mmol.) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (1.80 g., 9.4 mmol.) were added sequentially. After stirring at 0° C. for 30 minutes, the mixture was warmed to room temperature and stirred for 1.5 hours. The volatiles were evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed successively with 0.5 N hydrochloric acid, water, saturated sodium bicarbonate, and brine, and the organic layer was dried (sodium sulfate), filtered, and concentrated. The residue was flash chromatographed (Merck silica gel) eluting with 2:1 ethyl acetate/hexane to give 3.13 g. of title compound as a white foam. TLC (5% acetic acid in ethyl acetate) Rf =0.68.

後処理

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred for 1.5 hours
  3. customThe volatiles were evaporated
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed successively with 0.5 N hydrochloric acid, water, saturated sodium bicarbonate, and brine
  6. dry with materialthe organic layer was dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (Merck silica gel)
  10. washeluting with 2:1 ethyl acetate/hexane
  11. customto give 3.13 g

出典と根拠

ORDレコード
ord-075c8a8bd0d2438a82bc6f2098a3aa84
出典データセット
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05637698

反応ノート

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