Water → (3R)-1,8-Dithia-4-azaspiro[4.5]decane-3-carboxylic acid

HRID 279863Notes

Reaction equation

HRID 279863 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[S:8]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.O>C1(C)C=CC=CC=1>[S:4]1[C:11]2([CH2:12][CH2:13][S:8][CH2:9][CH2:10]2)[NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 5862L-(+)-CysteineHCID 534965Thiane 1-oxide

Product 1

HCID 13267688(3R)-1,8-Dithia-4-azaspiro[4.5]decane-3-carboxylic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.22 g of L-cysteine and 5 g of tetrahydrothiopyranone are suspended in 50 ml of toluene and the suspension is boiled, using a water separator, until the theoretical amount of water has been separated off. When the suspension is cooled, the product separates out as a light yellow precipitate, which is recrystallized from methanol/water to give 6.9 g of light yellow crystals of melting point 196° C.

Workup

  1. customuntil the theoretical amount of water has been separated off
  2. temperatureWhen the suspension is cooled
  3. customis recrystallized from methanol/water

Sources & evidence

ORD record
ord-af4a7eeebf2146d0bd9cc82797da849c
Source dataset
uspto-grants-1986_05
Patent number
US04587250

Reaction notes

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