Hydrochloric Acid → HCID 86675874, compound

HRID 1427794Notes

Reaction equation

HRID 1427794 reaction equation
CC1(C)C2CC[C@@]31[C@H](C2)N([C:12](=[O:23])[C@H:13]([CH3:22])[C@H:14]([O:19][CH2:20][CH3:21])[CH2:15][CH2:16][CH:17]=[CH2:18])S(=O)(=O)C3.[OH-:27].[Li+].Cl>O1CCCC1>[CH2:20]([O:19][C@H:14]([CH2:15][CH2:16][CH:17]=[CH2:18])[C@@H:13]([CH3:22])[C:12]([OH:23])=[O:27])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89393732HCID 89393732, compound

Product 1

HCID 86675874HCID 86675874, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,3R)-1-((1R,5S)-10,10-dimethyl-3,3-dioxo-3lambda*6*-thia-4-aza-tricyclo[5.2.1.0*1,5*]dec-4-yl)-3-ethoxy-2-methyl-hept-6-en-1-one (245 mg, 0.64 mmol) in tetrahydrofuran (12 mL) was added a lithium hydroxide solution (2 M aqueous, 5 mL). The mixture was heated to reflux for 16 hours then cooled to room temperature and acidified to pH 1 with 2 M hydrochloric acid (15 mL). The aqueous layer was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, filtered and evaporated to give a colourless gum, which was purified by silica gel chromatography using iso-hexanes/ether 1:1 to give the title compound (78 mg, 65%) as a colourless gum. 1H NMR (300 MHz, CDCl3) δ 1.17 (d, J=7.1 Hz, 3H), 1.20 (t, J=7.5 Hz, 3H), 1.55-1.65 (m, 2H), 2.05-2.30 (m, 2H), 2.72-2.83 (m, 1H), 3.52-3.62 (m, 3H), 4.95-5.10 (m, 2H), 5.75-5.90 (m, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a colourless gum, which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-da8eb996f0814242ae84b3fc0cf080dc
Source dataset
uspto-grants-2015_01
Patent number
US08933015B2

Reaction notes

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