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Lithium diisopropylamide → HCID 89463048、化合物

HRID 1473208
ノート
印刷プレビュー

反応式

HRID 1473208 の反応式
C([N:8]1[C:12]2[C:13](=[O:34])[N:14]([CH3:33])[C:15]([CH:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:25]([OH:27])=[O:26])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)C1C=CC=CC=1.[Li+].CC([N-]C(C)C)C.CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C>O1CCCC1>[C:29]([O:28][CH:24]([C:15]1[N:14]([CH3:33])[C:13](=[O:34])[C:12]2[NH:8][CH:9]=[CH:10][C:11]=2[C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1)[C:25]([OH:27])=[O:26])([CH3:32])([CH3:31])[CH3:30]
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

5

反応物 3

HCID 2724682Lithium diisopropylamide2 回HCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 71538481HCID 71538481、化合物

生成物 1

HCID 89463048HCID 89463048、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

An ice cold mixture of 2-(1-benzyl-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetic acid (200 mg, 0.423 mmol) in Tetrahydrofuran (THF) (2.0 mL) was treated with dropwise addition of LDA, 2M solution in heptane/THF/ethylbenzene (0.423 mL, 0.846 mmol) and then allowed to stir at 0° C. for 20 minutes. Additional LDA (0.212 mL, 0.423 mmol) was added and then stirred an additional 20 minutes. The mixture was quenched by adding 1N HCl, acidified to pH 2 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give the crude debenzylation product which was used crude in the next step. LC/MS (m/z) ES+=369 (M+1).

後処理

  1. stirringstirred an additional 20 minutes
  2. customThe mixture was quenched
  3. additionby adding 1N HCl
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude debenzylation product which

出典と根拠

ORDレコード
ord-f0b0812391a745cb9ba1dbd32b2d8426
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09012642B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート