Sodium Bicarbonate → HCID 13605510, compound

HRID 724547Notes

Reaction equation

HRID 724547 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 hours. The reaction mixture was added dropwise to NaHCO3 solution (2 mL, saturated) and then extracted with EtOAc (3 times). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by preparative TLC to provide the title compound (20 mg, 74% yield).

Workup

  1. extractionextracted with EtOAc (3 times)
  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-50110bad0af14591bfe008f94a77de9a
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

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