Hydrochloric Acid → 3-(4-Chloro-2,6-dimethyl-phenyl)-1,4-dihydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one

HRID 1473786노트

반응식

HRID 1473786 반응식
C[O:2][C:3]([C:5]1([N:13]([C:15](=[O:26])[CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=2[CH3:25])[OH:14])[CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]1)=O.CC(C)([O-])C.[K+].O.Cl>CN(C)C=O>[Cl:24][C:20]1[CH:19]=[C:18]([CH3:25])[C:17]([C:16]2[C:15](=[O:26])[N:13]([OH:14])[C:5]3([CH2:6][CH2:7][N:8]([O:11][CH3:12])[CH2:9][CH2:10]3)[C:3]=2[OH:2])=[C:22]([CH3:23])[CH:21]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 584280914-{[2-(4-Chloro-2,6-dimethyl-phenyl)-acetyl]-hydroxy-amino}-1-methoxy-piperidine-4-carboxylic acid methyl ester

생성물 1

HCID 584279803-(4-Chloro-2,6-dimethyl-phenyl)-1,4-dihydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 4-{[2-(4-chloro-2,6-dimethyl-phenyl)-acetyl]-hydroxy-amino}-1-methoxy-piperidine-4-carboxylic acid methyl ester (0.40 g, 1.04 mmol) in dimethylformamide (3 ml) at 0° C. was added potassium tert-butoxide (0.35 g, 3.12 mmol) in portions. After completion of the addition, stirring was continued at 0° C. for 30 minutes and at room temperature overnight. The reaction mixture was poured into cold water (0° C.), the pH adjusted to ca 5.5 by adding 1 N HCl and then thoroughly extracted with ethyl acetate (three times). The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated. The resulting crude material was purified by column chromatography on silica gel (gradient ethyl acetate/cyclohexane 1:1→ethyl acetate). Yield: 0.14 g of 3-(4-chloro-2,6-dimethyl-phenyl)-1,4-dihydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (compound P2ii.103) as a white solid.

후처리

  1. additionAfter completion of the addition
  2. extractionthoroughly extracted with ethyl acetate (three times)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting crude material was purified by column chromatography on silica gel (gradient ethyl acetate/cyclohexane 1:1→ethyl acetate)

출처 및 근거

ORD 기록
ord-c18f0769a7194aa1b04a2708d9725e87
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018135B2

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