Sodium Bicarbonate → HCID 70111769, compound

HRID 356168Notes

Reaction equation

HRID 356168 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([C:19](=[O:30])[CH2:20][NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]2[CH:31]=[CH:32][CH:33]=[CH:34][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:36]1([CH3:46])C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[OH:48].[Na+]>C(OC(=O)C)(=O)C>[C:36]([N:21]([CH2:20][C:19]([N:11]1[C@@H:12]2[CH2:18][CH2:17][CH2:16][C@@H:13]2[C:14](=[O:15])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:34]=[CH:33][CH:32]=[CH:31][C:10]1=2)=[O:30])[C:22](=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:48])[CH3:46]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 70111210HCID 70111210, compound

Product 1

HCID 70111769HCID 70111769, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of (3aR*,10aS*)-9-benzyl-4-(benzamidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (0.18 g, 0.4 mmol) in acetic anhydride (20 mL) was added 10 mg of p-toluenesulfonic acid monohydrate. The mixture was refluxed for two hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate, which was subjected to extraction with dichloromethane. The extract was washed with water, which was dried, followed by distilling off the solvent. The residue was purified silica-gel column chromatography (dichloromethane), followed by crystallization from diethylether to give 0.11 g (yield 58%) of the titled compound, m.p. 164-°166° C.

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. extractionwas subjected to extraction with dichloromethane
  3. washThe extract was washed with water, which
  4. customwas dried
  5. distillationby distilling off the solvent
  6. customThe residue was purified silica-gel column chromatography (dichloromethane)
  7. customfollowed by crystallization from diethylether

Sources & evidence

ORD record
ord-15c09a2bb916481ebf5f28b2697270b6
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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