Cesium carbonate → 2-(2,6-Dichloro-3-(2-pyrrolidinoethoxy)phenylcarbonyloxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide hydrochloride

HRID 743469ノート

反応式

HRID 743469 の反応式
[Cs+].[Cl:2][C:3]1[C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=[C:8]([Cl:20])[C:4]=1[C:5]([O-:7])=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:28][N:29]1[C:33](=[O:34])[CH:32]([CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[N:31]([CH3:40])[S:30]1(=[O:42])=[O:41]>CO>[ClH:2].[Cl:2][C:3]1[C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:10][CH:9]=[C:8]([Cl:20])[C:4]=1[C:5]([O:7][CH2:28][N:29]1[C:33](=[O:34])[CH:32]([CH2:35][CH2:36][CH:37]([CH3:38])[CH3:39])[N:31]([CH3:40])[S:30]1(=[O:41])=[O:42])=[O:6]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 15817425HCID 15817425、化合物HCID 88140560HCID 88140560、化合物

生成物 1

HCID 194244322-(2,6-Dichloro-3-(2-pyrrolidinoethoxy)phenylcarbonyloxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide hydrochloride

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2,6-dichloro-3-(2-pyrrolidinoethoxy)-benzoic acid cesium salt (prepared by reaction of the acid (1.045 g, 3.069 mmol) in 30 ml of methanol with Cs2CO3 (1.2 g) followed by removal of the solvent) in DMF was added 2-chloromethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.75 g; 1.86 mmol) at room temperature. The resulting solution was allowed to react at room temperature under nitrogen for 17 hours. The mixture was concentrated in vacuo and the residue was dissolved in 70% ethyl acetate in ether, filtered, and washed with sodium bicarbonate solution and dried over sodium sulfate. The organic solution was concentrated, the residual clear oil dissolved in 40 ml of ether and treated with ether/HCl. The salt was purified from methanol/ether to afford 2-(2,6-dichloro-3-(2-pyrrolidinoethoxy)phenylcarbonyloxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide hydrochloride (Formula I: Ar=2,6-Cl2 -3-(OCH2CH2 -1-pyrrolidinyl)phenyl; R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3 ; as HCl salt) a solid, m.p. 161°-162° C.

後処理

  1. customfollowed by removal of the solvent) in DMF
  2. customto react at room temperature under nitrogen for 17 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in 70% ethyl acetate in ether
  5. filtrationfiltered
  6. washwashed with sodium bicarbonate solution
  7. dry with materialdried over sodium sulfate
  8. concentrationThe organic solution was concentrated
  9. dissolutionthe residual clear oil dissolved in 40 ml of ether
  10. additiontreated with ether/HCl
  11. customThe salt was purified from methanol/ether

出典と根拠

ORDレコード
ord-622120d2b1194b51b07498678ab9fd84
出典データセット
uspto-grants-1996_09
特許番号
US05556909

反応ノート

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