Ammonium Chloride → HCID 57014599, compound

HRID 1655766Notes

Reaction equation

HRID 1655766 reaction equation
[C:1]1([C@H:7]([CH:10]([CH3:12])[CH3:11])[CH2:8]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].[C:14]([O:18][C:19]([NH:21][C@H:22]([CH:27]=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])([CH3:17])([CH3:16])[CH3:15].[Cl-].[NH4+]>O1CCCC1.BrCCBr.CCOCC>[OH:28][C@@H:27]([CH2:8][C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:10]([CH3:12])[CH3:11])[C@@H:22]([NH:21][C:19](=[O:20])[O:18][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 5462224MagnesiumHCID 53991717HCID 53991717, compound

Product 1

HCID 57014599HCID 57014599, compoundYield 42.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 78391,2-DibromoethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 40.9 g (0.18 mol) of (S)-(-)-2-phenyl-3-methylbromobutane in 110 ml of tetrahydrofuran and 0.5 ml of 1,2-dibromoethane was slowly added dropwise to a suspension of 6.6 g of magnesium in 25 ml of ether. The temperature rose to 50°. Thereafter, the reaction mixture was stirred at 50° for a further 2 hours and then cooled to -50°. Then, a solution of 13 g (0.06 mol) of N-t-butoxycarbonyl-L-leucinal in 40 ml of tetrahydrofuran was added slowly. After 16 hours at room temperature, the reaction mixture was treated with 200 ml of a 20% ammonium chloride solution. The organic phase was dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue (24.3 g) was chromatographed on silica gel with a 4:1 mixture of hexane and ether, to obtain 9.3 g of t-butyl [(1S,2S,4S)-2-hydroxy-1-isobutyl-5 -methyl-4-phenylhexyl]carbamate which has a melting point of 95°-96° after crystallization from hexane.

Workup

  1. customrose to 50°
  2. temperaturecooled to -50°
  3. waitAfter 16 hours at room temperature
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue (24.3 g) was chromatographed on silica gel with a 4:1 mixture of hexane and ether

Sources & evidence

ORD record
ord-dd9052d8ba0d4b97827a8e4b562cc087
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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