Ammonium Chloride → Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoate

HRID 1494103노트

반응식

HRID 1494103 반응식
[Cl-].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:3]=1.CC(C)([O-])C.[K+].[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH:49]([CH2:56][CH:57]=O)[CH2:50][CH2:51][C:52]([O:54][CH3:55])=[O:53])(=[O:43])=[O:42])=[CH:37][CH:36]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:34][C:35]1[CH:36]=[CH:37][C:38]([S:41]([NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH:49]([CH2:56][CH:57]=[CH:8][C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)[CH2:50][CH2:51][C:52]([O:54][CH3:55])=[O:53])(=[O:43])=[O:42])=[CH:39][CH:40]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 10340312Methyl 8-(p-chlorophenylsulfonamido)-4-(formylmethyl)octanoateHCID 22325077Triphenyl(3-pyridylmethyl)phosphonium chlorideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 54073742Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of 0.545 g of 3-pyridylmethyltriphenylphosphonium chloride in 6 mL tetrahydrofuran is added slowly 1.6 mL of 1.61 M potassium t-butoxide in tetrahydrofuran and the mixture is stirred at room temperature for 1 hour. A solution of 0.454 g of methyl 8-(p-chlorophenylsulfonamido)-4-(formylmethyl)octanoate in 1 mL tetrahydrofuran is added slowly and then stirred for 18 hours at room temperature. The reaction mixture is poured into saturated ammonium chloride and extracted with ethyl acetate (3×15 mL). The combined organic extracts are dried, filtered and evaporated to give a dark residue which is purified by flash chromatography to obtain, as a light amber oil, methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3- pyridyl)-2-propenyl]-octanoate. The product is a mixture of cis and trans isomers, the major component being the cis isomer. The above product is dissolved in 5 mL methylene chloride in a crystallizing dish and the solution is irradiated for 5 hours under UV light. The organic layer is diluted with methylene chloride and washed with aqueous sodium thiosulfate. The organic phase is dried, filtered and evaporated. The residue is purified by preparative thin layer chromatography to obtain a clear oil identified as about a 1:1 mixture of cis and trans isomers.

후처리

  1. stirringstirred for 18 hours at room temperature
  2. extractionextracted with ethyl acetate (3×15 mL)
  3. customThe combined organic extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. customto give a dark residue which
  7. customis purified by flash chromatography

출처 및 근거

ORD 기록
ord-f91b062409664becaee1bb4a2dad3185
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05025025

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