Hydrochloric Acid → 1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-ethoxycarbonylmethylthio-8-carboxymethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 458927ノート

反応式

HRID 458927 の反応式
[O:1]=[S:2]1(=[O:31])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][C:16]([OH:18])=[O:17])[C:11](Br)=[CH:12][C:7]=2[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5][C:4]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:25][CH3:26])[CH2:3]1.C([O-])([O-])=O.[Cs+].[Cs+].[C:38]([O:42][CH2:43][CH3:44])(=[O:41])[CH2:39][SH:40].Cl>O.CN(C=O)C>[O:1]=[S:2]1(=[O:31])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][C:16]([OH:18])=[O:17])[C:11]([S:40][CH2:39][C:38]([O:42][CH2:43][CH3:44])=[O:41])=[CH:12][C:7]=2[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5][C:4]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:25][CH3:26])[CH2:3]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 12185Ethyl ThioglycolateHCID 223931311,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-carboxymethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine

生成物 1

HCID 184424711,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-ethoxycarbonylmethylthio-8-carboxymethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine収率 100.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-carboxymethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 9; 50 mg, 0.098 mmol) and Cs2CO3 (51 mg, 0.15 mmol) were added to DMF (2.0 ml) and ethyl thioglycolate (0.02 ml, 0.15 mmol) was added. The reaction mixture was subjected to microwave irradiation in a Smith Synthesiser at 150° C. for 5 min. The reaction mixture was diluted with water (100 ml), made acidic with HCl (1 M), extracted with DCM (3×10 ml) and the collected organic layers were dried (MgSO4) to give the crude title compound (54 mg). M/z 550.2.

後処理

  1. additionwas added
  2. customirradiation in a Smith Synthesiser at 150° C. for 5 min
  3. extractionextracted with DCM (3×10 ml)
  4. dry with materialthe collected organic layers were dried (MgSO4)

出典と根拠

ORDレコード
ord-c6c3cb481ac0444cad8c4bcd2ffa9731
出典データセット
uspto-grants-2007_03
特許番号
US07192945B2

反応ノート

読み込み中…