Water → HCID 10839225, compound

HRID 2121233Notes

Reaction equation

HRID 2121233 reaction equation
C[O:2][C:3](=[O:36])[C@H:4]([CH2:32][CH2:33][S:34][CH3:35])[NH:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([F:30])([F:29])[F:28].[Li+].[OH-].O>C1COCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([NH:5][C@H:4]([C:3]([OH:36])=[O:2])[CH2:32][CH2:33][S:34][CH3:35])=[O:31])=[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:28])([F:29])[F:30])[CH:9]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 54291232HCID 54291232, compound

Product 1

HCID 10839225HCID 10839225, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 304F (291 mg, 0.56 mmol) was dissolved in THF(4 mL) and saturated aqueous LiOH (1 mL). Water (1 mL) was added and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was thoroughly evaporated and formic acid was added to pH3 The reaction was evaporated to dryness and ethyl acetate (10 mL) was added followed by a minimum quantity of H2O (−1 mL) to completely solubilize the free acid and the water soluble salts, respectively. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×). The ethyl acetate layers were combined and dried over Na2SO4, filtered, and evaporated and then lyophilized to give the title compound (242 mg, 86%) as an amorphous white solid. 1H NMR (300 MHz, CD3OD) δ 8.30 (bs, 1H), 8.14 (m, 1H), 7.76-7.33 (m, 9H), 5.28 (s, 2H), 4.87-4.40 (m, 1H), 2.40-2.06 (m, 2H), 2.04-1.94 (m, 4H contains methionine SMe), 1.92-1.80 (m, 1H). MS (CI) 505 (M+H)+ 505. Anal calcd for C25H23O4N2SF3: 0.65H2O solvate: C, 58.17; H, 4.74; N, 5.43. Found: C, 58.17; H, 4.80; N, 5.31. HRMS FAB Calcd m/z MH+ for C25H23O4N2SF3 505.1409, found 505.1408.

Workup

  1. customThe reaction mixture was thoroughly evaporated
  2. additionformic acid was added to pH3 The reaction
  3. customwas evaporated to dryness and ethyl acetate (10 mL)
  4. additionwas added
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-a6e35b95e24b417cbaa6e5beadc667c6
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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