Lithium Hydroxide → 5-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid

HRID 1848638ノート

反応式

HRID 1848638 の反応式
C(OC(CCC[O:11][C:12](=[O:32])[C:13]1[CH:18]=[C:17]([Br:19])[C:16]([Cl:20])=[CH:15][C:14]=1[O:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=O)(C)(C)C.[Li+].[OH-].OS([O-])(=O)=O.[Na+]>C1COCC1>[Br:19][C:17]1[C:16]([Cl:20])=[CH:15][C:14]([O:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])=[C:13]([CH:18]=1)[C:12]([OH:32])=[O:11]

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 686035915-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 3-tert-butoxycarbonyl-propyl ester

生成物 1

HCID 686032665-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid収率 41.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 5-bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 3-tert-butoxycarbonyl-propyl ester (8.2 g, 15.3 mmol) and LiOH (19.1 mL, 4 N, 76.6 mmol) in THF (150 mL) was stirred at rt for 16 hrs. The mixture was acidified by saturated NaHSO4 (50 mL) and extracted with ethyl acetate. The ethyl acetate layer was dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash chromatography (eluting with 50% ethyl acetate in hexane), followed by crystallization in hexane/ethyl acetate (10/1) to afford 5-bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid as white crystals (2.5 g). MS [M-(iso-butene+OH)]+: 320.8; tR=2.38 min. (method 1)

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via silica gel flash chromatography (eluting with 50% ethyl acetate in hexane)
  6. customfollowed by crystallization in hexane/ethyl acetate (10/1)

出典と根拠

ORDレコード
ord-87387904f7ba4ffaa599f0ff304bb6ea
出典データセット
uspto-grants-2015_02
特許番号
US08952161B2

反応ノート

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