Cysteamine → HCID 19992149, compound

HRID 345299Notes

Reaction equation

HRID 345299 reaction equation
[C:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[CH:14][C:15]([OH:17])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][CH2:19][CH2:20][SH:21]>CN(C)C=O.C(OCC)(=O)C>[C:1]1([CH2:7][CH:8]2[C:9]3([CH2:14][C:15](=[O:17])[NH:18][CH2:19][CH2:20][S:21]3)[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6058CysteamineHCID 54522509HCID 54522509, compound

Product 1

HCID 19992149HCID 19992149, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-phenylmethyl-1-carboxymethylenecyclohexane (10 g) and 2-aminoethanethiol (10 g) in N,N-dimethylformamide (10 ml) was refluxed for 20 hours under nitrogen atmosphere. The mixture was cooled to 0° C. and diluted with ethyl acetate (100 ml), and the mixture was washed with 1N hydrochloric acid (100 ml), water (100 ml), a saturated aqueous solution of sodium bicarbonte (100 ml) and brine (100 ml). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether to give 1-phenylmethyl-11-oxo-7-thia-10-azaspiro[5.6]dodecane (6.6 g).

Workup

  1. temperaturewas refluxed for 20 hours under nitrogen atmosphere
  2. washthe mixture was washed with 1N hydrochloric acid (100 ml), water (100 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-45a9cc542ad24e73943a4ad5996f67ac
Source dataset
uspto-grants-1991_10
Patent number
US05057513

Reaction notes

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