Trityl chloride → H-D-Cys(Trt)-OMe*HCl

HRID 1960428Notes

Reaction equation

HRID 1960428 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7][SH:8])[NH2:6].Cl.C(OCC)(=O)C.[C:17]([Cl:36])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)C>[ClH:36].[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7][S:8][C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[NH2:6]

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 516892Sodium BicarbonateHCID 637545D-Cysteine Methyl Ester HydrochlorideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 86619907H-D-Cys(Trt)-OMe*HClYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

D-Cysteine methyl ester hydrochloride (2.0 g) was suspended in N,N-dimethylformamide (12 mL), 4N hydrochloric acid/ethyl acetate solution (0.5 mL) was added, and the mixture was stirred at room temperature for 20 min. Trityl chloride (3.2 g) was added, and the mixture was stirred at 50° C. for 18 hr, diluted with diethyl ether, and poured into ice water. The mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO4), and concentrated. The obtained residue was diluted with ethyl acetate, and 4N hydrochloric acid/ethyl acetate solution (5 mL) was added. The precipitated solid was collected by filtration to give the title compound (3.0 g, yield 64%) as a colorless amorphous solid.

Workup

  1. stirringthe mixture was stirred at 50° C. for 18 hr
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. additionThe obtained residue was diluted with ethyl acetate, and 4N hydrochloric acid/ethyl acetate solution (5 mL)
  7. additionwas added
  8. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-b1e666cc18dd485c83dc18865f93f14f
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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