Ammonium Chloride → HCID 53694063, 화합물

HRID 1600844노트

반응식

HRID 1600844 반응식
[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@H:2]([C:6]([NH:8][C@H:9]([CH:17]=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])[CH:3]([CH3:5])[CH3:4].Cl[C:30]([F:42])([F:41])[C:31](=[O:40])[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Cl-].[NH4+]>C1COCC1.[Ti](Cl)(Cl)(Cl)Cl.[Zn]>[CH2:22]([O:21][C:19]([NH:1][C@H:2]([C:6]([NH:8][CH:9]([CH:17]([OH:18])[C:30]([F:41])([F:42])[C:31](=[O:40])[CH2:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

7

반응물 3

HCID 25517Ammonium ChlorideHCID 72430Mdl-28170HCID 11042220145299-85-0

생성물 1

HCID 53694063HCID 53694063, 화합물수율 61.1%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 24193Titanium Tetrachloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Add titanium tetrachloride (0.019 g, 0.1 eq) to a suspension of activated zinc (0.196 g, 3mAtg) in anhydrous THF (3 mL) at 0° C. under nitrogen. Stir 30 minutes and add CBz(L)-Val-Phe-H (0.42 g, 1.1 mmol), 1-chloro-1,1-difluoro-2-oxo-4-phenylbutane (0.218 g, 1.1 mmol), in anhydrous THF (4 mL). Allow the reaction to warm to room temperature and stir for 12 hours. Add a saturated solution of ammonium chloride (2 mL). Extract two times with diethyl ether (4 mL) and wash the organic phase with brine and dry over anhydrous magnesium sulphate. Concentrate the organic phase under vacuum. Purify the crude residue by flash chromatography (silica gel, 3:7 ethyl acetate:cyclohexane) to provide the title alcohol (0.381 g).

후처리

  1. customthe reaction
  2. stirringstir for 12 hours
  3. extractionExtract two times with diethyl ether (4 mL)
  4. washwash the organic phase with brine
  5. dry with materialdry over anhydrous magnesium sulphate
  6. concentrationConcentrate the organic phase under vacuum
  7. customPurify the crude residue by flash chromatography (silica gel, 3:7 ethyl acetate:cyclohexane)

출처 및 근거

ORD 기록
ord-82ba2768939e4a5ca3b6647503d9e0f7
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977074

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