Water → Fmoc-N-Me-Ser-OH

HRID 1482390ノート

反応式

HRID 1482390 の反応式
[C:1](Cl)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[CH3:19][NH:20][C@H:21]([C:24]([OH:26])=[O:25])[CH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCCC1.CCCCCC.C(OCC)C>[CH:16]1[C:17]2[CH:5]([CH2:4][O:3][C:1]([N:20]([CH3:19])[C@@H:21]([CH2:22][OH:23])[C:24]([OH:26])=[O:25])=[O:2])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 7009640Methylserine

生成物 1

HCID 11416557Fmoc-N-Me-Ser-OH

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

A solution of FmocCl (1.35 g, 5.21 mmol) in tetrahydrofuran (5 mL) was added to a solution of N-methyl-L-serine (Compound SP822) (621 mg, 5.21 mmol) and sodium carbonate (580 mg, 5.47 mmol) in tetrahydrofuran (15 mL)-water (20 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 20 minutes, followed by addition of diethyl ether (10 mL) and hexane (5 mL). The resulting mixture was extracted with water, and the aqueous layer was washed with ether (15 mL), followed by addition of concentrated hydrochloric acid (1 mL). The resulting mixture was extracted with ethyl acetate three times, and the organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The resulting crude product was purified by reverse-phase silica gel column chromatography (0.05% aqueous trifluoroacetic acid solution/0.05% trifluoroacetic acid-acetonitrile solution) to afford (Compound SP823) (1.49 g, 84%).

後処理

  1. extractionThe resulting mixture was extracted with water
  2. washthe aqueous layer was washed with ether (15 mL)
  3. additionfollowed by addition of concentrated hydrochloric acid (1 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate three times
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude product was purified by reverse-phase silica gel column chromatography (0.05% aqueous trifluoroacetic acid solution/0.05% trifluoroacetic acid-acetonitrile solution)
  8. customto afford (Compound SP823) (1.49 g, 84%)

出典と根拠

ORDレコード
ord-28f160afb2d8480881a35be2297cab18
出典データセット
uspto-grants-2016_08
特許番号
US09409952B2

反応ノート

読み込み中…