Sodium Bicarbonate → HCID 13605510, compound

HRID 724544Notes

Reaction equation

HRID 724544 reaction equation
O[C@@:2]12[CH2:22][CH2:21][CH:20]3[C:12]([C@@H:13]([C:28]4[CH:33]=[CH:32][C:31]([N:34](C)[C:35](=O)OC(C)(C)C)=[CH:30][CH:29]=4)[CH2:14][C@@:15]4([CH3:27])[CH:19]3[CH2:18][CH2:17][C@@:16]4([OH:26])[C:23]#[C:24][CH3:25])=[C:11]1[CH2:10][CH2:9][C:4]1(OCC[O:5]1)[CH2:3]2.CC1C=CC(S(O)(=O)=O)=CC=1.O.C(Cl)Cl.C1COCC1.C([O-])(O)=O.[Na+]>>[OH:26][C@:16]1([C:23]#[C:24][CH3:25])[CH2:17][CH2:18][C@H:19]2[C@H:20]3[C:12]([C@@H:13]([C:28]4[CH:29]=[CH:30][C:31]([NH:34][CH3:35])=[CH:32][CH:33]=4)[CH2:14][C@:15]12[CH3:27])=[C:11]1[C:2](=[CH:3][C:4](=[O:5])[CH2:9][CH2:10]1)[CH2:22][CH2:21]3

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 58743816HCID 58743816, compoundHCID 131726113HCID 131726113, compound

Product 1

HCID 13605510HCID 13605510, compoundYield 77.2%

Procedure

The compound of Example 1G (36 mg) was dissolved in 0.3 mL of a solution of TsOH.H2O/CH2Cl2/THF (1.9 g/3 mL/3.8 mL); the resultant mixture was stirred at room temperature for 3 hour. The reaction mixture was added dropwise to NaHCO3 solution (2 mL, saturated) and then extracted with EtOAc (3×). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by preparative TLC to provide the titled compound (20 mg, 74% yield).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-7c7a2171a7154d83877abdbce2442f7a
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

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