Water → HCID 18651235, compound

HRID 1609711Notes

Reaction equation

HRID 1609711 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([OH:14])[C@@H:10]([NH2:13])[CH2:11][OH:12])=[CH:5][CH:4]=1.[C:15]1(C)[CH:20]=CC=C[CH:16]=1.O>CC(C)=O>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]2[O:14][C:15]([CH3:20])([CH3:16])[NH:13][C@H:10]2[CH2:11][OH:12])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1140Toluene2×HCID 68816516854-32-3

Product 1

HCID 18651235HCID 18651235, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A stirred mixture of enantiomerically pure (+)-thiomicamine (100 g; 0.469 mol), toluene (920 ml) and acetone (100 ml) was heated at reflux for 18 hours beneath a Dean Stark trap: a mixture of toluene, water and acetone (11 g) was collected. The solvent (200 ml) was distilled at ambient pressure and then under vacuum (internal temperature 80° C.) to give compound 7 (118.6 g) as residue.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours beneath a Dean Stark trap
  3. customwas collected
  4. distillationThe solvent (200 ml) was distilled at ambient pressure

Sources & evidence

ORD record
ord-ad5b5b69c1424b6f87f7a794ac4e9f08
Source dataset
uspto-grants-1995_03
Patent number
US05401852

Reaction notes

Loading…