Methanesulfonic Acid → HCID 12071999, 화합물

HRID 49377

반응식

HRID 49377 반응식
C(OC(=O)[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.CS(O)(=O)=O.[OH-].[Na+]>C(Cl)Cl>[C:25]1([C:23]2[N:24]=[C:20]([C:17]3[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][NH2:10])=[CH:19][CH:18]=3)[S:21][CH:22]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

5

반응물 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 12071998Benzyl-{2-[4-(4-phenyl-thiazol-2-yl)-phenoxy]-ethyl}-carbamate

생성물 1

HCID 12071999HCID 12071999, 화합물수율 78%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Benzyl-{2-[4-(4-phenyl-thiazol-2-yl)-phenoxy]-ethyl}-carbamate (396 mg, 0.92 mmol) was dissolved in methylene chloride (4.6 ml) and methanesulfonic acid (0.895 ml, 13.8 mmol) was added dropwise to give a homogenous yellow solution. The reaction mixture was allowed to stir for about sixteen hours, diluted with methylene chloride, and was brought to basic pH (12-13) with 1M sodium hydroxide. The mixture was then extracted with methylene chloride, and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride) to afford the product in 78% yield (213 mg). LRMS ([M+H]+)=297.2.

후처리

  1. customto give a homogenous yellow solution
  2. extractionThe mixture was then extracted with methylene chloride
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude material was purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride)
  7. customto afford the product in 78% yield (213 mg)

출처 및 근거

ORD 기록
ord-a2226b9dd8a348c5915961ee284ee18f
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706743B2

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