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

HRID 2057884Notes

Reaction equation

HRID 2057884 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 h. Excess of solvent was evaporated under evaporator. Ethyl acetate 150 ml was added to the residue to give crystals. Crystals were recrystallized from ethyl acetate, mp. 91° C., yield 30%, IR (KBr) 1745 cm-1 ; NMR (CDCl3) δ 9.2-8.4 (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 h
  3. customExcess of solvent was evaporated under evaporator
  4. additionEthyl acetate 150 ml was added to the residue
  5. customto give crystals
  6. customCrystals were recrystallized from ethyl acetate, mp. 91° C., yield 30%, IR (KBr) 1745 cm-1

Sources & evidence

ORD record
ord-ba12b638ffc74bcba18d14acfcdb8ae8
Source dataset
uspto-grants-1980_07
Patent number
US04213978

Reaction notes

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