Phenol → [(R)-2-(7-nitro-5-phenoxymethyl-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid methyl ester

HRID 1045860노트

반응식

HRID 1045860 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:10][O:11][C:12](=[O:33])[CH2:13][C@@H:14]1[CH2:18][S:17][C:16]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28]Cl)=[CH:23][C:22]=3[N+:30]([O-:32])=[O:31])=[N:15]1.[NH4+].[Cl-]>CN(C=O)C>[CH3:10][O:11][C:12](=[O:33])[CH2:13][C@@H:14]1[CH2:18][S:17][C:16]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:23][C:22]=3[N+:30]([O-:32])=[O:31])=[N:15]1

참가 물질

6

반응물 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59543007(R)-2-[(5-chloromethyl-7-nitro-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]acetic acid methylester

생성물 1

HCID 59543026[(R)-2-(7-nitro-5-phenoxymethyl-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Phenol (192 mg, 2.04 mmol) was dissolved in DMF. NaH (60% mineral oil, 82 mg, 2.04 mmol) was added, and the reaction solution was cooled to 0° C. (R)-2-(5-chloromethyl-7-nitro-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl-acetic acid methyl ester (500 mg, 1.36 mmol) prepared in Preparation 42, which was dissolved in DMF, was slowly added thereto. The reaction solution was warmed to room temperature, and stirred for 4 h. After saturated aqueous NH4Cl solution was added to quench the reaction, the reaction mixture was extracted with EtOAc, dried over MgSO4, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (eluent: EtOAc/n-Hex=1/2) to give the title compound.

후처리

  1. customprepared in Preparation 42, which
  2. additionwas slowly added
  3. customto quench
  4. customthe reaction
  5. extractionthe reaction mixture was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography (eluent: EtOAc/n-Hex=1/2)

출처 및 근거

ORD 기록
ord-7f47025350914794a8683c7336a689d9
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569307B2

반응 노트

불러오는 중…