Acetic Acid → HCID 68547570, compound

HRID 2243492Notes

Reaction equation

HRID 2243492 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].FC(F)(F)C([O-])=O.[CH2:22]([O:24][C:25]([CH2:27][O:28][C:29]1[C:33]2[S:34][C:35]3[CH:36]=[C:37]([NH3+:41])[CH:38]=[CH:39][C:40]=3[C:32]=2[S:31][C:30]=1[C:42]([O:44][CH3:45])=[O:43])=[O:26])[CH3:23].[CH:46](=O)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C(O)(=O)C>ClCCCl.C(Cl)Cl>[CH3:45][O:44][C:42]([C:30]1[S:31][C:32]2[C:40]3[CH:39]=[CH:38][C:37]([NH:41][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:36][C:35]=3[S:34][C:33]=2[C:29]=1[O:28][CH2:27][C:25]([O:24][CH2:22][CH3:23])=[O:26])=[O:43]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68543319HCID 68543319, compound

Product 1

HCID 68547570HCID 68547570, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (90 mg, 0.42 mmol, 2.5 equiv) was added to a mixture of 1-ethoxycarbonylmethoxy-2-methoxycarbonyl-3,8-dithia-cyclopenta[a]inden-6-yl-ammonium trifluoroacetate (82 mg, 0.17 mmol), benzaldehyde (21 mg, 0.2 mmol, 1.2 equiv), and acetic acid (5wl) in DCE (4 ml). The reaction mixture was stirred at RT for 16 hr then DCM (20 ml) was added. The mixture was washed with sat. NaHCO3, dried over MgSO4, filtered, and the solvent was removed in vacuo. Purification by column chromatography yielded 61 mg (81%) of 6-benzylamino-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester.

Workup

  1. washThe mixture was washed with sat. NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-1c20eef2cd5741d28a7c4d395e2eb803
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

Loading…