Sodium Hydroxide → 945635-15-4

HRID 2190356Notes

Reaction equation

HRID 2190356 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:9]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:8][CH:7]=[CH:6][C:5]=1[C:21]1[S:22][CH2:23][C@:24]([CH3:31])([C:26]([O:28]CC)=[O:27])[N:25]=1>CO>[OH:3][C:4]1[C:9]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:8][CH:7]=[CH:6][C:5]=1[C:21]1[S:22][CH2:23][C@:24]([CH3:31])([C:26]([OH:28])=[O:27])[N:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135611042HCID 135611042, compound

Product 1

HCID 135565672945635-15-4Yield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 50% (w/w) NaOH (13.88 mL, 266.02 mmol) in CH3OH (120 mL) was added to 13 (8.89 g, 20.80 mmol) in CH3OH (280 mL) with ice bath cooling. The reaction mixture was stirred at room temperature for 6 h, and the bulk of the solvent was removed by rotary evaporation. The residue was treated with dilute NaCl (300 mL) and the basic aqueous phase was cooled in ice, acidified with 2 N HCl to pH=2, and extracted with EtOAc (4×150 mL). After the EtOAc layers were washed with saturated NaCl (300 mL), glassware that was presoaked in 3 N HCl for 15 min was employed henceforth. After solvent removal by rotary evaporation, purification was done on C-18 reverse phase column, eluting with 50% aq. methanol and lyophilized to furnish 4.98 g of 9 (60%) as an orange oil: [α]20+61.9°; 1H NMR (D2O) δ 1.77 (s, 3H), 3.35 (s, 3H), 3.56-3.62 (m, 3H), 3.64-3.73 (m, 4H), 3.75-3.89 (m, 2H), 3.92-3.96 (m, 2H), 3.99 (d, 1H, J=11.6), 4.25-4.31 (m, 2H), 6.99 (t, 1H, J=8.2), 7.26-7.33 (m, 2H); 13C NMR δ 24.52, 39.93, 59.07, 69.04, 69.83, 70.49, 70.64, 70.86, 71.97, 83.21, 116.33, 117.94, 118.50, 122.80, 147.67, 150.24, 172.38, 176.10; HRMS m/z calcd for C18H26NO7S, 400.1429 (M+H). found, 400.1413.

Workup

  1. temperaturecooling
  2. customthe bulk of the solvent was removed by rotary evaporation
  3. additionThe residue was treated with dilute NaCl (300 mL)
  4. temperaturethe basic aqueous phase was cooled in ice
  5. extractionextracted with EtOAc (4×150 mL)
  6. washAfter the EtOAc layers were washed with saturated NaCl (300 mL), glassware that
  7. waitwas presoaked in 3 N HCl for 15 min
  8. customAfter solvent removal
  9. customby rotary evaporation, purification
  10. washeluting with 50% aq. methanol

Sources & evidence

ORD record
ord-5f65bc82c0bc4697a23749bf65824a06
Source dataset
uspto-grants-2012_12
Patent number
US08324397B2

Reaction notes

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