1-Butanol → L-Cysteine, butyl ester, hydrochloride (1:1)

HRID 1277932Notes

Reaction equation

HRID 1277932 reaction equation
[ClH:1].[NH2:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][SH:5].[CH2:9](O)[CH2:10][CH2:11][CH3:12]>Cl>[ClH:1].[CH2:9]([O:7][C:6](=[O:8])[C@H:3]([CH2:4][SH:5])[NH2:2])[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 2631-ButanolHCID 60960Cysteine Hydrochloride

Product 1

HCID 86737879L-Cysteine, butyl ester, hydrochloride (1:1)Yield 30%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

L-Cysteine hydrochloride (100 g) is dissolved in 250 ml of butanol saturated with dry HCl. The solution is heated under reflux for 4 hours. Excess solvent is evaporated and ethyl acetate (150 ml) is added to the residue. The crystals which form are recrystallized from ethyl acetate, mp 91° C., yield 30%, IR (KBr)1745 cm-1 ; NMR (CDCl3) δ9.2-3.4 (b, 3, NH3⊕), 4.7 (t, 1, --CH), 4.3 (t, 2, --OCH2 --), 3.3 (b, 2, CH2S), 1.0 (5, 3, --CH3), 1.0-3.0 (m, 4, --CH2CH2).

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for 4 hours
  3. customExcess solvent is evaporated
  4. additionethyl acetate (150 ml) is added to the residue
  5. customThe crystals which form are recrystallized from ethyl acetate, mp 91° C., yield 30%, IR (KBr)1745 cm-1

Sources & evidence

ORD record
ord-76b75c4256c94ef4abb8c98b2c26ab79
Source dataset
uspto-grants-1981_07
Patent number
US04279900

Reaction notes

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