Nitrogen → (S)-3-[3-(5-Bromo-2-dimethylcarbamoylsulfanyl-3-nitro-benzyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747487ノート

反応式

HRID 1747487 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([S:11][C:12](=[O:16])[N:13]([CH3:15])[CH3:14])=[C:4]([CH2:17]O)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:38]([O:40][C:41](=[O:57])[CH2:42][C@@H:43]([N:47]1[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=2[NH:49][C:48]1=[O:56])[CH2:44][CH2:45][CH3:46])[CH3:39].N#N.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:38]([O:40][C:41](=[O:57])[CH2:42][C@@H:43]([N:47]1[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=2[N:49]([CH2:17][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]=2[S:11][C:12](=[O:16])[N:13]([CH3:14])[CH3:15])[C:48]1=[O:56])[CH2:44][CH2:45][CH3:46])[CH3:39]

参加物

7

反応物 5

HCID 947NitrogenHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59497467(S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 59497682Dimethyl-thiocarbamic acid S-(4-bromo-2-hydroxymethyl-6-nitro-phenyl)ester

生成物 1

HCID 59497582(S)-3-[3-(5-Bromo-2-dimethylcarbamoylsulfanyl-3-nitro-benzyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester収率 37.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Dimethyl-thiocarbamic acid S-(4-bromo-2-hydroxymethyl-6-nitro-phenyl) ester (250 mg, 0.74 mmol), triphenylphosphine (215 mg, 0.82 mmol) and (S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (303 mg, 0.82 mmol,) are added to a flask with a N2 line. Dry THF (6 mL) is added and the reaction is cooled to 0° C. DIAD (1 ml of THF, 0.82 mmol) is added dropwise over the course of 5 minutes to the reaction and the reaction is warmed slowly to room temperature. The reaction is stirred for 1 hour then evaporated in vacuo and directly purified on silica gel with dichloromethane methanol as the eluent. Reaction is re-purified via-preparative LC/MS to give 166 mg (37%) of the desired compound. LCMS (ESMS): m/z 594.4 (M+H+).

後処理

  1. temperaturethe reaction is warmed slowly to room temperature
  2. customthen evaporated in vacuo
  3. customdirectly purified on silica gel with dichloromethane methanol as the eluent
  4. customReaction
  5. customis re-purified via-preparative LC/MS

出典と根拠

ORDレコード
ord-edbd7430bcbd4b40ab1d657aa90fe941
出典データセット
uspto-grants-2015_10
特許番号
US09150556B2

反応ノート

読み込み中…