Trityl chloride → amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane

HRID 847577Notes

Reaction equation

HRID 847577 reaction equation
CN[C@H](C(N[C@H:13]([C@@H:21]([OH:27])[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=O)CC1N=CNC=1.C([N:30](CC)CC)C.C(Cl)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[NH2:30][CH:14]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:13][C@@H:21]([OH:27])[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178484877HCID 178484877, compound

Product 1

HCID 57008919amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptaneYield 270.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2(S)-(Nα -methyl-L-histidyl)amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (900 mg) and triethylamine (494 mg) in methylene chloride (20 ml) was added trityl chloride (696 mg) at 0° C. The mixture was stirred at the same temperature for 1 hour. After evaporation of the solvent, the residue was dissolved in ethyl acetate (30 ml) and the solution was washed with 1 M sodium bicarbonate solution and water successively, and dried over magnesium sulfate. Evaporation of the solvent gave 2(S)-(Nα -methyl-Nim -trityl-L-histidyl)amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (1.46 g) as an amorphous powder.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  3. washthe solution was washed with 1 M sodium bicarbonate solution and water successively
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-48824f44281345e5bb6236fb8f9cc779
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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