Sodium Bicarbonate → 6-(5-{1-[3-chloro-4-(methylsulfonyl)phenyl]-2-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]ethyl}-1H-pyrrol-2-yl)pyridine-3-carbaldehyde

HRID 1882084Notes

Reaction equation

HRID 1882084 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:30][C@H:31]2[CH2:51][CH2:50][C:33]3([O:37][C@H:36]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C@@H:35]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[O:34]3)[CH2:32]2)[C:13](=O)[CH2:14][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[O:28]CCO3)=[CH:20][N:19]=2)=O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C([O-])(=O)C.[NH4+:56].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([C:13]2[NH:56][C:16]([C:18]3[N:19]=[CH:20][C:21]([CH:24]=[O:28])=[CH:22][CH:23]=3)=[CH:15][CH:14]=2)[CH2:30][C@H:31]2[CH2:51][CH2:50][C:33]3([O:37][C@H:36]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C@@H:35]([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[O:34]3)[CH2:32]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 593312385-[3-chloro-4-(methylsulfonyl)phenyl]-1-[5-(1,3-dioxolan-2-yl)pyridin-2-yl]-6-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]hexane-1,4-dione

Product 1

HCID 593315026-(5-{1-[3-chloro-4-(methylsulfonyl)phenyl]-2-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]ethyl}-1H-pyrrol-2-yl)pyridine-3-carbaldehydeYield 32%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-[3-chloro-4-(methylsulfonyl)phenyl]-1-[5-(1,3-dioxolan-2-yl)pyridin-2-yl]-6-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]hexane-1,4-dione (276 mg) in acetic acid (2 mL) was added ammonium acetate (466 mg), and the mixture was stirred at 110° C. for 1 hr. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (80.0 mg, yield 32%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d7509ada2ef444fa9807a6e44d8e0281
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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