Hydrochloric Acid → HCID 86736267, compound

HRID 2163824Notes

Reaction equation

HRID 2163824 reaction equation
[S:1]1[C:5]2([CH2:10][CH2:9][S:8][CH2:7][CH2:6]2)[CH:4]([C:11]([O:13]CC)=[O:12])[N:3]=C1.[ClH:16]>>[ClH:16].[NH2:3][CH:4]([C:5]1([SH:1])[CH2:6][CH2:7][S:8][CH2:9][CH2:10]1)[C:11]([OH:13])=[O:12]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 22749586HCID 22749586, compound

Product 1

HCID 86736267HCID 86736267, compoundYield 100%

Procedure

27.2 g (0.11 mole) of ethyl 1,8-dithia-3-azaspiro[4.5]dec-2-ene-4-carboxylate are dissolved in 865 ml of 6N hydrochloric acid and boiled under reflux for 5 hours. The reaction mixture is then concentrated in vacuo in a rotary evaporator. The residue is taken up several times in dry benzene to eliminate traces of water and is then triturated in diethyl ether and filtered. There are obtained 27 g (approx. 100% of theory) of alpha-amino-4-mercapto-2,3,5,6-tetrahydro-4H-thiopyran-4-acetic acid hydrochloride. The product gives a straight spot by thin layer chromatography on silica (eluent: butanol, acetic acid, water: 4:1:1; Rf=0.45); M.P. 193 -197° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationThe reaction mixture is then concentrated in vacuo in a rotary evaporator
  3. customis then triturated in diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-03078b9fb01e4ce2931da5d8050de3a6
Source dataset
uspto-grants-1979_01
Patent number
US04137236

Reaction notes

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