Triethylamine → Boc-His(Ts) 3-cyclohexylalaninal

HRID 1614059Notes

Reaction equation

HRID 1614059 reaction equation
[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:19]([OH:21])=[O:20])[CH2:3][C:4]1[N:8]=[CH:7][N:6]([S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=1.[CH:29]1([CH2:35][C@@H:36]([CH2:38][OH:39])[NH2:37])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(N(CC)CC)C>CS(C)=O>[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:19]([OH:21])=[O:20])[CH2:3][C:4]1[N:8]=[CH:7][N:6]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH3:16])=[CH:17][CH:18]=2)(=[O:11])=[O:10])[CH:5]=1.[CH:29]1([CH2:35][C@@H:36]([CH:38]=[O:39])[NH2:37])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 131717821Boc-His(Ts) 3-cyclohexyl-alaninol

Product 1

HCID 131717823Boc-His(Ts) 3-cyclohexylalaninalYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a mixture of the dipeptide alcohol [18a] (2.0 g, 3.65 mmol), triethylamine (1.30 g, 12.85 mmol, 3.5 eq) and DMSO (6 ml) is added at room temperature SO3 ·pyridine (2.03 g, 12.75 mmol, 3.5 eq) in DMSO (6 ml) and the mixture is stirred for 35 minutes. The reaction mixture is poured on ice, and the resultant aqueous mixture is extracted with ethyl acetate (20 ml×3). The organic layer is subsequently washed with 10% aqueous citric acid, saturated aqueous sodium chloride (×2), 7% aqueous sodium bicarbonate, and saturated aqueous sodium chloride, dried over MgSO4, and concentrated to dryness in vacuo. The resultant residue is purified with silica gel chromatography (SiO2 :100 g, CH2Cl2 :MeOH=95:5) to obtain Boc-His(Ts)-3-cyclohexylalaninal [14a] (1.67 g, 84%) in amorphous powder.

Workup

  1. additionThe reaction mixture is poured on ice
  2. extractionthe resultant aqueous mixture is extracted with ethyl acetate (20 ml×3)
  3. washThe organic layer is subsequently washed with 10% aqueous citric acid, saturated aqueous sodium chloride (×2), 7% aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness in vacuo
  6. customThe resultant residue is purified with silica gel chromatography (SiO2 :100 g, CH2Cl2 :MeOH=95:5)

Sources & evidence

ORD record
ord-6eae773efdb64156a8214ad68d647d14
Source dataset
uspto-grants-1993_03
Patent number
US05194608

Reaction notes

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