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

HRID 2286830Notes

Reaction equation

HRID 2286830 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) was dissolved in 250 ml of butanol saturated with dry HCl. The solution was heated under reflux for 4 hours. Excess of solvent was evaporated under evaporator. Ethyl acetate (150 ml) was added to the residue to give crystals. The crystals were recrystallized from ethyl acetate, mp 91° C., yield 30%, IR (KBr) 1745 cm-1 ; NMR (CDCl3) δ9.2-8.4 (b, 3, NH3⊕), 4.7 (t, 1, --CH), 4.3 (t, 2-, --CH2)--,, 3.3 (b, 2, CH2S), 1.0 (t, 3, --CH3 --), 1.0-3.0 (m, 4, --CH2CH2).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 4 hours
  3. customExcess of solvent was evaporated under evaporator
  4. additionEthyl acetate (150 ml) was added to the residue
  5. customto give crystals
  6. customThe crystals were recrystallized from ethyl acetate, mp 91° C., yield 30%, IR (KBr) 1745 cm-1

Sources & evidence

ORD record
ord-41b349214aa4427cbc6094476bb50908
Source dataset
uspto-grants-1981_05
Patent number
US04268441

Reaction notes

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