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Hydrochloric Acid → HCID 53707024、化合物

HRID 1789813
ノート
印刷プレビュー

反応式

HRID 1789813 の反応式
ClC(OC)=O.[C:6]([O:10][C:11](=[O:32])[C:12]([CH2:17][C:18]1[CH:19]=[N:20][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:22][CH:23]=1)([CH3:16])[C:13](O)=[O:14])([CH3:9])([CH3:8])[CH3:7].CCN(CC)CC.[BH4-].[Na+].Cl>C1COCC1.CCOC(C)=O>[C:6]([O:10][C:11](=[O:32])[C:12]([CH2:13][OH:14])([CH3:16])[CH2:17][C:18]1[CH:19]=[N:20][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:22][CH:23]=1)([CH3:7])([CH3:9])[CH3:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 54536141HCID 54536141、化合物

生成物 1

HCID 53707024HCID 53707024、化合物収率 57%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8857Ethyl Acetate溶媒

実験手順

Methyl chloroformate (75 μL, 0.92 mmol) was added dropwise to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-methyl-malonic acid mono-tert-butyl ester (348 mg, 0.915 mmol) and Et3N (123 μL, 0.92 mmol) in THF (6 mL). The reaction mixture was stirred for 20 min., filtered and added dropwise to a suspension of NaBH4 (39 mg, 1.04 mmol) in THF (6 mL) at 0° C. The reaction was stirred for 16 h at room temperature. 0.2 M HCl was added followed by EtOAc. The organic phase was washed with brine and dried. Concentration under reduced pressure followed by chromathography (toluene/EtOAc, 3:1→1:3) gave 3-(6tert-butoxycarbonylamino-pyridin-3-yl)-2-hydroxymethyl-2-methyl-propionic acid tert-butyl ester (190 mg, 57%).

後処理

  1. filtrationfiltered
  2. stirringThe reaction was stirred for 16 h at room temperature
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationConcentration under reduced pressure

出典と根拠

ORDレコード
ord-33705ed7c39b4002b3186b0f5b799ade
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07071175B1

反応ノート

読み込み中…

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