Sodium Hydroxide → S-[2-(1-benzyloxycarbonyl-4-piperidyl)ethyl]-L-cysteine

HRID 1638988Notes

Reaction equation

HRID 1638988 reaction equation
O.Cl.[NH2:3][C@H:4]([C:7]([OH:9])=[O:8])[CH2:5][SH:6].[OH-].[Na+].[CH2:12]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29]I)[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[CH2:12]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][S:6][CH2:5][C@@H:4]([C:7]([OH:9])=[O:8])[NH2:3])[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23462L-Cysteine hydrochloride monohydrateHCID 14600697Benzyl 4-(2-iodoethyl)piperidine-1-carboxylate

Product 1

HCID 14600699S-[2-(1-benzyloxycarbonyl-4-piperidyl)ethyl]-L-cysteineYield 68.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a nitrogen gas flow, 562 mg of L-cysteine hydrochloride monohydrate is dissolved in an aqueous solution of 2N sodium hydroxide. To the resulting solution, 5 ml of a tetrohydrofuran solution containing 1.2 g of 2-(1-benzyloxycarbonyl-4-piperidyl)ethyl iodide is added, and stirred for 1.5 hours at room temperature. Then, 3 ml of ethanol is further added, and stirred for 2 hours. The reaction solvent is distilled off under reduced pressure. To the residue, water and ether are added, and the mixture is shaken. The water layer is separated and adjusted to pH 5 with 2N aqueous hydrochloric acid to precipitate crystals. The crystals are recrystallized from methanol to give 0.8 g of S-[2-(1-benzyloxycarbonyl-4-piperidyl)ethyl]-L-cysteine having a melting point of 185° to 188° C.

Workup

  1. additionis added
  2. stirringstirred for 2 hours
  3. distillationThe reaction solvent is distilled off under reduced pressure
  4. additionTo the residue, water and ether are added
  5. stirringthe mixture is shaken
  6. customThe water layer is separated
  7. customto precipitate crystals
  8. customThe crystals are recrystallized from methanol

Sources & evidence

ORD record
ord-a4b00b691d984251b8563c73cf233717
Source dataset
uspto-grants-1989_11
Patent number
US04882326

Reaction notes

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