Water → HCID 58503177, compound

HRID 446783Notes

Reaction equation

HRID 446783 reaction equation
[N:1]([CH2:4][C@@H:5]([F:17])[C@H:6]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:7]=C)=[N+:2]=[N-:3].C(O)(C(F)(F)F)=[O:19].[OH2:25]>O1CCOCC1.CCOC(C)=O>[N:1]([CH2:4][C@@H:5]([F:17])[C@H:6]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:19])=[O:25])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 58503258HCID 58503258, compound

Product 1

HCID 58503177HCID 58503177, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 4 (51.2 g, 32.5 mmol) in dioxane (600 ml) was added a solution of TFA (16.02 ml, 208 mmol) in water (200 ml) and the reaction was heated at 50° C. for 17 hours. The reaction mixture was diluted with EtOAc (800 mL) and washed with sat. aq. NaHCO3 (2×800 mL), brine (400 mL), dried over MgSO4, filtered and concentrated under vacuum to yield 5 (49.9 g, 32.5 mmol, 100% yield): MS m/z calcd for C78H82N6O24 (M+Na+) 1509.5. found 1509.3.

Workup

  1. washwashed with sat. aq. NaHCO3 (2×800 mL), brine (400 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8ec35befe9aa449389b8a0d2f6a2f4f5
Source dataset
uspto-grants-2013_07
Patent number
US08481502B2

Reaction notes

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