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

HRID 618137노트

반응식

HRID 618137 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-15 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f1d65958061f47adb2585230fd7f2675
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952306

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