Ammonium Chloride → HCID 53694063, compound

HRID 1600844Notes

Reaction equation

HRID 1600844 reaction equation
[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

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 724302-{[(Benzyloxy)(hydroxy)methylidene]amino}-3-methyl-N-(1-oxo-3-phenylpropan-2-yl)butanimidic acidHCID 11042220145299-85-0

Product 1

HCID 53694063HCID 53694063, compoundYield 61.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-82ba2768939e4a5ca3b6647503d9e0f7
Source dataset
uspto-grants-1999_11
Patent number
US05977074

Reaction notes

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