Acetic Acid → HCID 68544557, compound

HRID 2243493Notes

Reaction equation

HRID 2243493 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].[O:46]1[CH2:51][CH2:50][C:49](=O)[CH2:48][CH2:47]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][CH:49]4[CH2:50][CH2:51][O:46][CH2:47][CH2:48]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 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 68543319HCID 68543319, compound

Product 1

HCID 68544557HCID 68544557, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

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 (85 mg, 0.17 mmol), tetrahydropyran-4-one (24 μl, 0.2 mmol, 1.2 equiv), and acetic acid (5 μl) in DCE (4 ml) and stirred at 50° C. for 17 hr. DCM (20 ml) was added and the mixture was washed with sat. NaHCO3, dried over MgSO4, filtered, and the solvent was reoved in vacuo. Purification by column chromatography yielded 72 mg (94%) of 1-ethoxycarbonylmethoxy-6-(tetrahydropyran-4-ylamino)-3,8-dithiacyclopenta[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. customPurification by column chromatography

Sources & evidence

ORD record
ord-e91f40dbed9d4efbbd2fc0cbfe3ee795
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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