1,2-Dichloroethane → 4-(2-Aminothiazol-4-yl)butanoyl-glycyl-2(S)-phenylsulfonamido-beta-alanine t-butyl ester

HRID 618137ノート

反応式

HRID 618137 の反応式
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[N:7]=1.FC(F)(F)C(O)=O.[C:21]([O:25][C:26](=[O:44])[C@@H:27]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:28][NH:29][C:30](=[O:33])[CH2:31][NH2:32])([CH3:24])([CH3:23])[CH3:22].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[C:21]([O:25][C:26](=[O:44])[C@@H:27]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:28][NH:29][C:30](=[O:33])[CH2:31][NH:32][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][C:6]1[N:7]=[C:3]([NH2:2])[S:4][CH:5]=1)([CH3:24])([CH3:22])[CH3:23]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 867544654-(2-Aminothiazol-4-yl)butanoic acid hydrochlorideHCID 86754466Glycyl-2(s)-phenylsulfonamido-beta-alanine t-butyl ester trifluoroacetate salt

生成物 1

HCID 867544694-(2-Aminothiazol-4-yl)butanoyl-glycyl-2(S)-phenylsulfonamido-beta-alanine t-butyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-15 °C

実験手順

Acid 1-4 (300 mg, 1.35 mmol), amine 1-7 (600 mg, 1.37 mmol), HOBT (219 mg, 1.14 mmol) and NMM (445 μL, 4.04 mmol) were combined in 13 mL DMF, cooled to -15° C., and EDC (310 mg, 1.61 mmol) was added. The reaction was warmed to RT, stirred overnight, then diluted with EtOAc, washed with water, sat. NaHCO3, and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, 20% MeOH/EtOAc) provided 1-8 as yellow solid.

後処理

  1. temperatureThe reaction was warmed to RT
  2. washwashed with water, sat. NaHCO3, and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-f1d65958061f47adb2585230fd7f2675
出典データセット
uspto-grants-1999_09
特許番号
US05952306

反応ノート

読み込み中…