Hydrochloric Acid → HCID 53744040, compound

HRID 5417Notes

Reaction equation

HRID 5417 reaction equation
[C:1]([CH:4]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][S:9][CH2:8][C@@H:7]([C:17]([OH:19])=[O:18])[NH:6][C:5]1=[O:20])(O)=O.N1CCCCC1.C=O.Cl>N1C=CC=CC=1>[CH2:1]=[C:4]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][S:9][CH2:8][C@@H:7]([C:17]([OH:19])=[O:18])[NH:6][C:5]1=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 54274042(3R)-6-carboxy-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid

Product 1

HCID 53744040HCID 53744040, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

(3R)-6-Carboxy-5-oxo-1-thia-4-azacyclotridecane -3-carboxylic acid (1.71 g, 5.64 mmol) is dissolved in pyridine (20 ml) and piperidine (0.096 g, 1.13 mmol) is added followed by paraformaldehyde (0.25 g, 8.46 mmol). The mixture is heated to 65° C. and stirred for 2 hours. The mixture is cooled to room temperature, poured into 6N hydrochloric acid (100 ml) and extracted with ethyl acetate (2×100 ml). The combined extracts are washed with brine (1×100 ml), dried (MgSO4) and solvent is evaporated to give (3R)-6-methylidene-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid, m.p. 184°-186° C.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined extracts are washed with brine (1×100 ml)
  4. dry with materialdried (MgSO4) and solvent
  5. customis evaporated

Sources & evidence

ORD record
ord-65e3bf11fde04d758153eba4550a656c
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Reaction notes

Loading…