Fumaric Acid → HCID 86743816, compound

HRID 1165766Notes

Reaction equation

HRID 1165766 reaction equation
C([O:4][C@@H:5]1[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[S:10][C:9]2[C:20]3[C:25]([CH:26]=[CH:27][C:8]=2[N:7]([CH2:28][CH2:29][NH:30][CH3:31])[C:6]1=[O:32])=[CH:24][CH:23]=[CH:22][CH:21]=3)(=O)C.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>C(O)C.C([O-])([O-])=O.[K+].[K+].C(#N)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[OH:4][C@@H:5]1[C@H:11]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[S:10][C:9]2[C:20]3[C:25]([CH:26]=[CH:27][C:8]=2[N:7]([CH2:28][CH2:29][NH:30][CH3:31])[C:6]1=[O:32])=[CH:24][CH:23]=[CH:22][CH:21]=3

Participants

6

Reactant 2

HCID 444972Fumaric AcidHCID 54208628HCID 54208628, compound

Product 1

HCID 86743816HCID 86743816, compoundYield 53.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 11430Potassium CarbonateSolvent

Procedure

A solution of 0.4 g (0.00089 mol) of (+)-cis-3-(acetyloxy)-2,3-dihydro-2-(4-methoxyphenyl)-5-[2-(methylamino)ethyl]naphtho[1,2-b][1,4]thiazepin-4(5H)-one in a mixture of 10 ml of ethanol and 10 ml of 0.5M K2CO3 was heated at 70°-80° for one hour. The mixture was concentrated to a low volume under reduced pressure, diluted with water (saturated with NaCl) and extracted with ethyl acetate. The combined ethyl acetate solutions were washed with brine, dried (MgSO4) and the solvent was removed. The residue, 0.25 g in acetonitrile, was treated with 0.08 g (0.0069 mol) of fumaric acid and the crystals were collected to afford 0.25 g (53%) of (+)-cis-2,3-dihydro-3-hydroxy-5-[2-(methylamino)ethyl]-2-(4-methoxyphenyl)naphtho[1,2-b][1,4]thiazepin-4(5H)-one (E)-2-butenedioate as the semihydrate, mp 178°-180° [α]D 25 +7.97° (C. 0.966, MeOH).

Workup

  1. temperaturewas heated at 70°-80° for one hour
  2. concentrationThe mixture was concentrated to a low volume under reduced pressure
  3. additiondiluted with water (saturated with NaCl)
  4. extractionextracted with ethyl acetate
  5. washThe combined ethyl acetate solutions were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent was removed
  8. customthe crystals were collected

Sources & evidence

ORD record
ord-765de39a75c941bb80f79a0fe57a2169
Source dataset
uspto-grants-1990_03
Patent number
US04912102

Reaction notes

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