Hydrochloric Acid → HCID 7009563, compound

HRID 336444Notes

Reaction equation

HRID 336444 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.Cl.[NH2:12][C@H:13]([C:16]([OH:18])=[O:17])[CH2:14][SH:15].[OH-].[Na+]>C(OCC)C.C(O)C>[NH2:12][C@@H:13]([CH2:14][S:15][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:16]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 5862L-(+)-CysteineHCID 77384-Methoxybenzyl alcoholHCID 14798Sodium Hydroxide

Product 1

HCID 7009563HCID 7009563, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

4-Methoxybenzyl alcohol (280 g, 1780 mmol) dissolved in diethylether (400 mL) was added in drops to a mixture of diethylether (400 mL) and conc. hydrochloric acid (400 mL) over 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 mL) to ethanol (1890 mL). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction mixture was cooled to 0° C., and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered and dried to give the title compound (250 g, Yield 64%).

Workup

  1. customThe organic layer was separated
  2. additionadded to a solution
  3. customprepared
  4. stirringThe mixture was stirred for 2 h at room temperature
  5. customAfter completion of the reaction
  6. filtrationThe resulting solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-c304752165c843c6aa8a8518ec87586f
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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