Sodium Sulfite → HCID 67248533, compound

HRID 410467Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[C:9]([OH:18])([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)[CH2:8][CH:7]1[CH3:19])=[O:5])[CH3:2].[Br:20]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[C:9]([C:13]2[S:14][C:15]([Br:20])=[CH:16][N:17]=2)([OH:18])[CH2:8][CH:7]1[CH3:19])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of the product of Step 1 (3.84 g, 8.54 mmol) in dimethylformamide (33.5 mL) was added N-bromosuccinimide (1.75 g, 9.82 mmol) and the solution stirred at 55° C. for 3 hours. A solution of sodium sulfite (0.538 g, 4.27 mmol) in water (60 mL) was added dropwise to the reaction. The mixture was diluted with ethyl acetate (100 mL) and washed the organic extract with water (2×100 mL). The combined aqueous layers were back extracted with ethyl acetate (3×100 mL) and the combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography provided a solid, which was triturated with hexanes, to give 4-(5-bromo-thiazol-2-yl)-4-hydroxy-2,5-dimethyl-cyclohexanecarboxylic acid ethyl ester (1.07 g, 2.95 mmol). MS ESI: [M]+ m/z 362.1.

Workup

washwashed the
extractionorganic extract with water (2×100 mL)
extractionThe combined aqueous layers were back extracted with ethyl acetate (3×100 mL)
dry with materialthe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography
customprovided a solid, which
customwas triturated with hexanes

Sources & evidence

ORD record: ord-2f5e5980dbf1411bbd8b904a49c6163e
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759366B2

Reaction notes

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