Cesium carbonate → HCID 10357872, compound

HRID 1796875Notes

Reaction equation

HRID 1796875 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][CH2:14][S:15][CH2:16][CH3:17])[CH:11]([C:18]([OH:20])=[O:19])[O:10]C1(C)C)=O)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].[C:29]([O:35][CH2:36]Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]>CN(C=O)C.C(OCC)(=O)C>[NH2:8][C@H:12]([CH2:13][CH2:14][S:15][CH2:16][CH3:17])[CH:11]([OH:10])[C:18]([O:20][CH2:36][O:35][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:19]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 87885Chloromethyl pivalateHCID 91593982HCID 91593982, compound

Product 1

HCID 10357872HCID 10357872, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 22B (0.102 g, 0.31 mmol), cesium carbonate (0.111 g, 0.34 mmol), and chloromethyl pivalate (0.055 mL, 0.38 mmol) in DMF (3 mL) at room temperature was stirred for 24 hours, diluted with ethyl acetate, washed sequentially with water, aqueous NaHCO3, pH 7 buffer, and brine, dried (MgSO4), filtered, and concentrated. The residue was dissolved in 4M HCl in dioxane (2 mL), stirred for 1 hour, treated with water (1 mL), stirred for 1 hour, concentrated, and purified by reverse phase HPLC with acetonitrile/water to provide the desired product. MS (ESI) m/e 308 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 7.87–7.80 (br s, 2H), 6.53 (m, 0.7H), 6.33 (d, 0.3H), 4.40 (m, 0.3H), 4.24 (m, 0.7H), 4.28 (s, 0.6H), 4.26 (s, 1.4H), 3.53 (m, 1H), 2.63 (m, 2H), 2.48 (m, 2H), 1.90–1.75 (m, 2H), 1.22–1.16 (m, 12H).

Workup

  1. washwashed sequentially with water, aqueous NaHCO3, pH 7 buffer
  2. dry with materialbrine, dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 4M HCl in dioxane (2 mL)
  6. additiontreated with water (1 mL)
  7. stirringstirred for 1 hour
  8. concentrationconcentrated
  9. custompurified by reverse phase HPLC with acetonitrile/water

Sources & evidence

ORD record
ord-69551f0660ce4041add72a0e7715921c
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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