Hydrochloric Acid → HCID 7009563, compound

HRID 1802809Notes

Reaction equation

HRID 1802809 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1.[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][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([O:3][CH3:2])=[CH:5][CH:6]=1)[C:16]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 5862L-(+)-CysteineHCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 7009563HCID 7009563, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixed solution of diethyl ether (400 ml) and conc. hydrochloric acid (400 ml) was added in drops 4-methoxybenzyl chloride (280 g, 1780 mmol) dissolved in diethyl ether (400 ml) for 2 h, and the mixture was stirred for 1 h. The organic layer was separated and added to a solution which was prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 ml) in ethanol (1890 ml). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the 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 (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid (250 g, 1035 mmol, Yield 64%).

Workup

  1. customThe organic layer was separated
  2. additionadded to a solution which
  3. customwas prepared
  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-f9dfc1746374498f96c3eee2a0ceb540
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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