Sodium Hydroxide → HCID 135611041, compound

HRID 705417Notes

Reaction equation

HRID 705417 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:6][C:5]=1[C:21]1[S:22][CH2:23][C@:24]([CH3:32])([C:26]([O:28]C(C)C)=[O:27])[N:25]=1>CO>[OH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:6][C:5]=1[C:21]1[S:22][CH2:23][C@:24]([CH3:32])([C:26]([OH:28])=[O:27])[N:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135611040HCID 135611040, compound

Product 1

HCID 135611041HCID 135611041, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 50% (w/w) NaOH (3.34 mL, 94 mmol) in CH3OH (34 mL) was added to 12 (2.14 g, 4.85 mmol) in CH3OH (70 mL) with ice bath cooling. The reaction mixture was stirred at room temperature for 18 h, and the bulk of the solvent was removed by rotary evaporation. The residue was treated with dilute NaCl (100 mL) and was extracted with ether (3×50 mL). The basic aqueous phase was cooled in ice, acidified with 2 N HCl to pH=2, and extracted with EtOAc (3×100 mL). After the EtOAc layers were washed with saturated NaCl (100 mL), glassware that was presoaked in 3 N HCl for 15 min was employed henceforth. After solvent removal by rotary evaporation, 1.88 g of 6 (97%) was obtained as an orange oil: [α]20 +40.0°; 1H NMR (D2O) δ 1.72 (s, 3H), 3.26 (d, 1H, J=11.2), 3.38 (s, 3H), 3.54-3.58 (m, 2H), 3.64-3.71 (m, 4H), 3.72-3.76 (m, 2H), 4.07-4.11 (m, 3H), 6.91-6.95 (m, 2H), 7.01 (dd, 1H, J=9.0, 3.0); 13C NMR δ 24.46, 40.04, 59.04, 68.40, 69.86, 70.48, 70.62, 70.80, 71.91, 83.44, 115.21, 115.65, 118.09, 121.63, 151.12, 153.69, 171.83, 176.18; HRMS m/z calcd for C18H26NO7S, 400.1429 (M+H). found, 400.1416.

Workup

  1. temperaturecooling
  2. customthe bulk of the solvent was removed by rotary evaporation
  3. additionThe residue was treated with dilute NaCl (100 mL)
  4. extractionwas extracted with ether (3×50 mL)
  5. temperatureThe basic aqueous phase was cooled in ice
  6. extractionextracted with EtOAc (3×100 mL)
  7. washAfter the EtOAc layers were washed with saturated NaCl (100 mL), glassware that
  8. waitwas presoaked in 3 N HCl for 15 min
  9. customAfter solvent removal
  10. customby rotary evaporation

Sources & evidence

ORD record
ord-792bbffc6e7e4cbeb85f2fdd9d6e207d
Source dataset
uspto-grants-2015_11
Patent number
US09174948B2

Reaction notes

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