Hydrochloric Acid → HCID 86754565, compound

HRID 1277934Notes

Reaction equation

HRID 1277934 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[ClH:19]>C(OCC)(=O)C>[ClH:19].[CH2:8]([O:6][C:5](=[O:7])[C@H:2]([CH2:3][SH:4])[NH2:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5862L-(+)-CysteineHCID 81741-Decanol

Product 1

HCID 86754565HCID 86754565, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

L-Cysteine (157.4 g) is added to 250 ml of decyl alcohol saturated with dry HCl. The mixture is heated to 150° C. for 6 hours. The solution is cooled and then is mixed with an equal volume of ethyl acetate. The solution is cooled in a dry ice bath to give crystals. The crystals are filtered and are recrystallized from ethyl acetate, mp 96°-99° C., yield 100 g, IR (KBr) 1745 cm-1 ; NMR (CDCl3) δ8.4-9.2 (b, 3, NH330 ), 4.7 (t, 1, --CH--), 4.3 (t, 2, --OCH2 --), 3.4 (b, 2, --CH2S--), 1.0--3.0 (m, 16 --(CH2)8 --), 2.6-2.8 (b, 1, SH), 1.0 (t, 3, CH3 --).

Workup

  1. temperatureThe solution is cooled
  2. temperatureThe solution is cooled in a dry ice bath
  3. customto give crystals
  4. filtrationThe crystals are filtered
  5. customare recrystallized from ethyl acetate, mp 96°-99° C., yield 100 g, IR (KBr) 1745 cm-1

Sources & evidence

ORD record
ord-7b3858966ea74390a7f66c6cfb3f1feb
Source dataset
uspto-grants-1981_07
Patent number
US04279900

Reaction notes

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