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

HRID 1588837Notes

Reaction equation

HRID 1588837 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 1M 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 1M sodium bicarbonate solution and water successively
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e872da4d504e4814920e4bfff05e998a
Source dataset
uspto-grants-1993_06
Patent number
US05223489

Reaction notes

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