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Diisopropylethylamine → 5-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid 1-tert-butyl ester 3-(2,5-dioxo-pyrrolidin-1-yl) ester

HRID 444987
ノート
印刷プレビュー

反応式

HRID 444987 の反応式
[C:1]([O:5][C:6](=[O:40])[C:7]1[CH:15]=[C:14]([NH:16][C:17](=[O:39])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:54]1[C:59](=[O:60])[CH2:58][CH2:57][C:55]1=[O:56])=[N+](C)C)C.CCN(C(C)C)C(C)C>C1COCC1>[O:56]=[C:55]1[CH2:57][CH2:58][C:59](=[O:60])[N:54]1[O:11][C:10](=[O:12])[C:9]1[CH:8]=[C:7]([CH:15]=[C:14]([NH:16][C:17](=[O:39])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:13]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 667245005-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid mono-tert-butyl ester

生成物 1

HCID 871256345-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid 1-tert-butyl ester 3-(2,5-dioxo-pyrrolidin-1-yl) ester

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

5-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid mono-tert-butyl ester (140 mg, 0.25 mmol) was dissolved in dry THF (3.5 ml). TSTU (95 mg, 0.30 mmol) and DIPEA (70 ul, 0.30 mmol) were added. The mixture was stirred at RT under nitrogen over the week-end. The reaction mixture was almost dry. EtOAc was added and the precipitate was removed by filtration. The filtrate was extracted with 0.1 N HCl (2×), brine (1×), dried (Na2SO4) and concentrated to give the title compound as a syrup containing a trace of an impurity in a quantitative yield (0.165 mg).

後処理

  1. customThe reaction mixture was almost dry
  2. additionEtOAc was added
  3. customthe precipitate was removed by filtration
  4. extractionThe filtrate was extracted with 0.1 N HCl (2×), brine (1×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3952a3c47a4d442bba89141f86fddeb0
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08476228B2

反応ノート

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