Hydrochloric Acid → HCID 22940519, compound

HRID 1174378Notes

Reaction equation

HRID 1174378 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[OH-].[Na+].[CH3:10]I.Cl[C:13]([O:15][CH3:16])=[O:14].Cl>CO>[CH3:16][O:15][C:13]([NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4][CH3:10])=[O:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5862L-(+)-CysteineHCID 6328Methyl iodideHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide2×

Product 1

HCID 22940519HCID 22940519, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of L-cysteine (50 mg, 0.413 mmol) in methanol (0.4 mL) was treated with 1N NaOH (0.45 mL, 0.45 mmol) and methyl iodide (28.3 μL, 0.45 mmol) at 0° C. The mixture was warmed to 25° C. over 16 h, recooled to 0° C., and treated with 3N NaOH (0.45 μL, 1.3 mmol) and methyl chloroformate (64 μL, 0.83 mmol) at 25° C. for 4 h. The mixture was acidified with 2N HCl, and partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, and dried over MgSO4 and filtered. The solvents were evaporated to give the crude title compound (60 mg, 75%).

Workup

  1. customrecooled to 0° C.
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvents were evaporated

Sources & evidence

ORD record
ord-e02375f08d614508b0ded4ae5871421a
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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