Water → ethyl 2-[2-(Boc-L-alanyl)aminothiazol-4-yl]glyoxylate

HRID 274241

反応式

HRID 274241 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[C:14]([NH:21][C@H:22]([C:24](O)=[O:25])[CH3:23])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].Cl.C(N=C=NCCCN(C)C)C.O>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:14]([NH:21][C@H:22]([C:24]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)=[O:25])[CH3:23])([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15]

参加物

7

反応物 4

HCID 962WaterHCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4356513Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetate

生成物 1

HCID 18659161ethyl 2-[2-(Boc-L-alanyl)aminothiazol-4-yl]glyoxylate収率 71.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

Ethyl 2-(2-aminothiazol-4-yl)glyoxylate (4.0 g) and Boc-L-alanine (5.67 g) were dissolved in 40 ml of N,N-dimethylformamide (hereafter abbreviated as DMF), and thereto was added 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (5.74 g) under ice-cooling followed by addition of 4-dimethylaminopyridine (0.4 g). The mixture was stirred at room temperature for 5 hours. Water (400 ml) was added thereto, and the mixture was extracted twice with ethyl acetate (300 ml). The ethyl acetate layer was washed with 10% aqueous solution of citric acid (200 ml), saturated aqueous solution of sodium bicarbonate (200 ml) and saturated brine (200 ml) in this order, and dried over anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography eluted with benzene-ethyl acetate. The object fraction was concentrated to give 5.30 g of ethyl 2-[2-(Boc-L-alanyl)aminothiazol-4-yl]glyoxylate.

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted twice with ethyl acetate (300 ml)
  3. washThe ethyl acetate layer was washed with 10% aqueous solution of citric acid (200 ml), saturated aqueous solution of sodium bicarbonate (200 ml) and saturated brine (200 ml) in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe ethyl acetate was distilled off under reduced pressure
  6. washeluted with benzene-ethyl acetate
  7. concentrationThe object fraction was concentrated

出典と根拠

ORDレコード
ord-f36417eb0f2945ac991ee10e1df38efd
出典データセット
uspto-grants-1995_02
特許番号
US05389625

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