Hydrochloric Acid → 4-[1-(3-bromo-4-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic Acid tert-butyl Ester

HRID 456524노트

반응식

HRID 456524 반응식
Cl.[OH-:2].[NH4+:3].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:19]2[S:20][CH:21]=[C:22]([CH3:25])[C:23]=2[Br:24])=O)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].Cl>N1C=CC=CC=1>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:19]2[S:20][CH:21]=[C:22]([CH3:25])[C:23]=2[Br:24])=[N:3][OH:2])[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 13908798HCID 13908798, 화합물HCID 588177114-[1-(3-Bromo-4-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 724345734-[1-(3-bromo-4-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic Acid tert-butyl Ester수율 23.7%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
70 °C

실험 절차

Add ammonium hydroxide hydrochloride (50.68 mmol, 3.52 g, 2.00 equivalents) to a stirred solution of 4-[1-(3-bromo-4-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester (25.54 mol, 9.84 g, 1.00 equivalents) in pyridine (47.5 mL). Stir at room temperature overnight and at 70° C. for 4 hours. Cool the reaction mixture and add hydrochloric acid (3 M solution, 115 mL). Extract the reaction mixture with dichloromethane (115 mL), filter the organic layer, wash with water (100 mL), dry over magnesium sulfate, filter and evaporate. Recrystallize the resulting residue from toluene to yield a white solid (4.84 g). LC/MS (APCI), m/e 403 (MH+), retention time 2 min. 32 sec. Condition I.

후처리

  1. temperatureCool the reaction mixture
  2. extractionExtract the reaction mixture with dichloromethane (115 mL)
  3. filtrationfilter the organic layer
  4. washwash with water (100 mL)
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. customevaporate
  8. customRecrystallize the resulting residue from toluene

출처 및 근거

ORD 기록
ord-a4c08d3300a647d4ba825fffd3ff538f
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186724B2

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