Homoveratrylamine → N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)-m-dithiane-2-propionamide

HRID 616311

반응식

HRID 616311 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:17][CH2:18][C:19]([OH:21])=O)[S:16][CH2:15][CH2:14][CH2:13][S:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.ClC(O)=O.[CH2:33]([NH2:45])[CH2:34][C:35]1[CH:44]=[CH:43][C:40]([O:41][CH3:42])=[C:37]([O:38][CH3:39])[CH:36]=1>O1CCCC1>[CH3:39][O:38][C:37]1[CH:36]=[C:35]([CH:44]=[CH:43][C:40]=1[O:41][CH3:42])[CH2:34][CH2:33][NH:45][C:19](=[O:21])[CH2:18][CH2:17][C:11]1([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[S:12][CH2:13][CH2:14][CH2:15][S:16]1

참가 물질

6

반응물 4

HCID 8421HomoveratrylamineHCID 8471TriethylamineHCID 164602Chloroformic acidHCID 227583982-(3,4-Dimethoxyphenyl)-m-dithiane-2-propionic acid

생성물 1

HCID 22758395N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)-m-dithiane-2-propionamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

13.2 g of 2-(3,4-dimethoxyphenyl)-m-dithiane-2-propionic acid, 4 g of triethylamine and 180 ml of tetrahydrofuran are cooled to 0° C and treated dropwise within 10 minutes with 5.44 g of chloroformic acid is isobutyl ester in 80 ml of tertrahydrofuran. The mixture is then held at room temperature for 3 hours and treated at 0° C with 7.25 g of homoveratrylamine in 40 ml of tetrahydrofuran. The suspension is left to stand at 3° C for 48 hours, then evaporated, treated with water and extracted with ether/methylene chloride (3:1). The ethereal extracts are washed with water, sodium bicarbonate solution, 1-N tartaric acid and water. The organic phase is dried over magnesium sulphate and evaporated. The residue is crystallized from methylene chloride/ether at 0° C. There is obtained N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)-m-dithiane-2-propionamide of melting point 135°-136° C.

후처리

  1. waitThe suspension is left
  2. waitto stand at 3° C for 48 hours
  3. customevaporated
  4. additiontreated with water
  5. extractionextracted with ether/methylene chloride (3:1)
  6. washThe ethereal extracts are washed with water, sodium bicarbonate solution, 1-N tartaric acid and water
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. customevaporated
  9. customThe residue is crystallized from methylene chloride/ether at 0° C

출처 및 근거

ORD 기록
ord-53e5182be45341b1bb7db93ab86ebea3
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04073797

연결된 노트

불러오는 중…