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Diisopropylethylamine → (3s)-3-(Benzo[1,3]dioxol-5-yl)-3-((5-(2-methoxycarbonyl-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester

HRID 431513
ノート
印刷プレビュー

反応式

HRID 431513 の反応式
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=1)=[O:4].[C:15]([O:19][C:20](=[O:33])[CH2:21][C@H:22]([NH2:32])[C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=1)([CH3:18])([CH3:17])[CH3:16].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(C(C)C)CC)(C)C>CN(C)C=O.ClCCl>[C:15]([O:19][C:20](=[O:33])[CH2:21][C@@H:22]([C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=1)[NH:32][C:12]([C:10]1[S:11][C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:8][CH:9]=1)=[O:14])([CH3:18])([CH3:16])[CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 108676335-(2-Methoxycarbonyl-ethyl)-thiophene-2-carboxylic acidHCID 57048399tert-butyl (3S)-3-amino-3-(1,3-dioxaindan-5-yl)propanoate

生成物 1

HCID 57125533(3s)-3-(Benzo[1,3]dioxol-5-yl)-3-((5-(2-methoxycarbonyl-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester
収率 130%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

214 mg (1 mmol) of 5-(2-methoxycarbonyl-ethyl)-thiophene-2-carboxylic acid (example 1, step b) were dissolved in 5 ml of anhydrous dimethylformamide. 265 mg (1 mmol) of (3S)-3-amino-3-(benzo[1,3]dioxol-5-yl)-propionic acid tert-butyl ester and 328 mg (1 mmol) of TOTU were added, and 3 mmol (0.51 ml) of N,N-diisopropyl-N-ethylamine were added to keep the pH of the mixture at 7.5 to 8. The reaction mixture was stirred for 4.5 hours at room temperature. Solvents were removed under reduced pressure to give a dark brown oil. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution, 10% citric acid and with water. Then the organic phase was dried with anhydrous magnesium sulfate. After filtration the solvents were removed in vacuo to give 600 mg of a brownish oil which was purified by chromatography (silica gel; ethyl acetate/heptane (1/2, v/v)). 425 mg of a resin were obtained.

後処理

  1. customSolvents were removed under reduced pressure
  2. customto give a dark brown oil
  3. washwashed with saturated sodium bicarbonate solution, 10% citric acid and with water
  4. dry with materialThen the organic phase was dried with anhydrous magnesium sulfate
  5. filtrationAfter filtration the solvents
  6. customwere removed in vacuo

出典と根拠

ORDレコード
ord-a56cfa7264714c18829d69bb4f8af3b1
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06660728B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート