Sodium borohydride → 2-{2-[(tert-Butoxycarbonyl)amino]ethoxy}-5-chloro-3-(1-hydroxyethyl)-6-methylbenzoic acid

HRID 626823ノート

反応式

HRID 626823 の反応式
[BH4-].[Na+].[C:3]([C:6]1[C:7]([O:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:8]([C:12]([CH3:16])=[C:13]([Cl:15])[CH:14]=1)[C:9]([OH:11])=[O:10])(=[O:5])[CH3:4]>CO>[C:24]([O:23][C:21]([NH:20][CH2:19][CH2:18][O:17][C:7]1[C:6]([CH:3]([OH:5])[CH3:4])=[CH:14][C:13]([Cl:15])=[C:12]([CH3:16])[C:8]=1[C:9]([OH:11])=[O:10])=[O:22])([CH3:25])([CH3:27])[CH3:26]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866975173-Acetyl-2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-5-chloro-6-methylbenzoic acid

生成物 1

HCID 866975182-{2-[(tert-Butoxycarbonyl)amino]ethoxy}-5-chloro-3-(1-hydroxyethyl)-6-methylbenzoic acid収率 80.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium tetrahydroborate (6.1 mg, 0.16 mmol) was added to a mixture of 3-acetyl-2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-5-chloro-6-methylbenzoic acid (40 mg, 0.1 mmol) in methanol (0.50 mL) at 0° C. and the reaction was stirred at room temperature for 1 hour. The solvent was removed and the residue was diluted with ethyl acetate, washed with saturated sodium bicarbonate, adjusted the pH to 5 with 1 N hydrogen chloride solution, washed with brine, dried over sodium sulfate, filtered and concentrated to give the desired compound (30 mg, 70%). LCMS calculated for C17H24ClNO6Na (M+Na)+: m/z=396.1; found: 396.0.

後処理

  1. customThe solvent was removed
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-e4c65447b7b04ed284bfe0d2a824a45a
出典データセット
uspto-grants-2016_04
特許番号
US09309251B2

反応ノート

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