Sodium Bicarbonate → HCID 10622632, compound

HRID 1016266Notes

Reaction equation

HRID 1016266 reaction equation
[C:1]([O:4][C@H:5]1[C:10](=[CH:11][O:12]CC)[CH2:9][C@H:8]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:6]12[CH3:7])[C:23]1[CH:22]=[CH:21][C:20]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:19][C:18]=1[CH2:17][CH2:16]3)(=[O:3])[CH3:2].C([O-])(O)=O.[Na+]>C1COCC1.Cl.O>[C:1]([O:4][C@H:5]1[C@H:10]([CH:11]=[O:12])[CH2:9][C@H:8]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:6]12[CH3:7])[C:23]1[CH:22]=[CH:21][C:20]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:19][C:18]=1[CH2:17][CH2:16]3)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 86585978HCID 86585978, compound

Product 1

HCID 10622632HCID 10622632, compoundYield 56.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 183 mg (0.397 mmol) of 4 in THF (1.5 mL) with 4 drops of 10% aqueous HCl and 2 drops of H2O was stirred at rt for 6 h. Reaction was poured into saturated aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (3×, 75 mL). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo. Purification of the residue by repeated (3×) flash chromatography on a 2×15 cm column of silica gel using hexanes/acetone (6:1) as eluent gave 96.9 mg (56%) of 5 as a white solid. Data for 5: TLC, T-3, Rf0.22. 1H NMR (500 MHz, CDCl3) δ 0.91 (s, 3H, H-18), 2.10 (s, 3H, OAc), 4.86 (d, 1H, J=8.1 Hz, H-17), 5.04 (s, 2H, benzylic), 6.73 (d, 1H, J=2.7 Hz, H-4), 6.79 (dd, 1H, J=8.5, 2.7 Hz, H-2), 7.19 (d, 1H, J=8.5 Hz, H-1), 7.31-7.44 (m, 5H, Ar—H), 9.83 (d, 1H, J=3.1 Hz, O═CH); HRMS (ES) calcd for C28H32O4Na (M+Na+) m/e 455.2198, found m/e 455.2205.

Workup

  1. customReaction
  2. extractionextracted with CH2Cl2 (3×, 75 mL)
  3. dry with materialCombined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue

Sources & evidence

ORD record
ord-b0f06e2beff4437a9e31f51bded855d4
Source dataset
uspto-grants-2002_11
Patent number
US06476012B2

Reaction notes

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