Sodium hydride → (S)-3-Butyloxy-4-(2-pyrrolidinylmethoxy)-1,2,5-thiadiazole

HRID 264805

反応式

HRID 264805 の反応式
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])=O)CCC.[H-].[Na+].[CH2:17]([O:21][C:22]1[C:26](S(C)(=O)=O)=[N:25][S:24][N:23]=1)[CH2:18][CH2:19][CH3:20]>C1COCC1>[CH2:17]([O:21][C:22]1[C:26]([O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[N:25][S:24][N:23]=1)[CH2:18][CH2:19][CH3:20]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 196003073-Butyloxy-4-methanesulfonyl-1,2,5-thiadiazoleHCID 53961054(S)-1-butyloxycarbonyl-2-pyrrolidinemethanol

生成物 1

HCID 53691159(S)-3-Butyloxy-4-(2-pyrrolidinylmethoxy)-1,2,5-thiadiazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of (S)-1-butyloxycarbonyl-2-pyrrolidinemethanol (1.21, 0.006 mol) in THF (5 mL) was added to a suspension of 60% NaH in oil (0.24 g, 0.006 mol) in THF (30 mL). After 1 h, the mixture was heated to gentle reflux for 1 h. To the solution was added 3-butyloxy-4-methanesulfonyl-1,2,5-thiadiazole (1 g, 0.0042 mol) and the reaction heated to reflux overnight. The solvent was evaporated, the residue treated with cold H2O, and the mixture extracted with EtOAc. The extracts were dried and treated with a stream of dry HCl for 3 min. After another hour, the solvent was evaporated, the residue treated with cold H2O, and the mixture extracted with ether. The aqueous fraction was made basic and extracted with EtOAc. The extracts were washed with water, dried, and the solvent evaporated to give a liquid. The HCl salt (0.72 g) crystallized from EtOAc, m.p. 99°-100° C. (Compound 32).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto gentle reflux for 1 h
  3. temperaturethe reaction heated
  4. temperatureto reflux overnight
  5. customThe solvent was evaporated
  6. additionthe residue treated with cold H2O
  7. extractionthe mixture extracted with EtOAc
  8. customThe extracts were dried
  9. additiontreated with a stream of dry HCl for 3 min
  10. waitAfter another hour
  11. customthe solvent was evaporated
  12. additionthe residue treated with cold H2O
  13. extractionthe mixture extracted with ether
  14. extractionextracted with EtOAc
  15. washThe extracts were washed with water
  16. customdried
  17. customthe solvent evaporated
  18. customto give a liquid
  19. customThe HCl salt (0.72 g) crystallized from EtOAc, m.p. 99°-100° C. (Compound 32)

出典と根拠

ORDレコード
ord-49ff137d70e2447f8b1e1bdea649ec63
出典データセット
uspto-grants-1997_07
特許番号
US05646289

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