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

HRID 626823노트

반응식

HRID 626823 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e4c65447b7b04ed284bfe0d2a824a45a
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309251B2

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