Ammonium Chloride → HCID 53694063、化合物

HRID 1600844ノート

反応式

HRID 1600844 の反応式
[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

参加物

7

反応物 3

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

生成物 1

HCID 53694063HCID 53694063、化合物収率 61.1%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 24193Titanium Tetrachloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-82ba2768939e4a5ca3b6647503d9e0f7
出典データセット
uspto-grants-1999_11
特許番号
US05977074

反応ノート

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