Water → HCID 58503177, compound

HRID 446784Notes

Reaction equation

HRID 446784 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]>CC(O)=O.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 962Water2×HCID 6422Trifluoroacetic acid4×HCID 58503258HCID 58503258, compound

Product 1

HCID 58503177HCID 58503177, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a stirring solution of 4 (9.1 g, 4.76 mmol) in AcOH (19.8 mL) was added TFA (1.8 mL of a 3:1 TFA:water solution), and the reaction was heated at 40° C. for 45 min. Additional TFA (0.45 mL of a 3:1 TFA:water solution) was added and the reaction was heated for 1.5 hr. The reaction was then cooled to room temperature, diluted with EtOAc (200 mL) and washed with sat. aq. NaHCO3 (3×200 mL) and brine (200 mL). The organic layer was dried over Na2SO4, filtered and concentrated to dryness to yield compound 5 (8.7 g, 3.43 mmol), which was carried through to the next step without further purification. MS m/z calcd for C99H111N5O25Si2 (M+Na+) 1848.7. found 1848.3.

Workup

  1. temperaturethe reaction was heated for 1.5 hr
  2. temperatureThe reaction was then cooled to room temperature
  3. washwashed with sat. aq. NaHCO3 (3×200 mL) and brine (200 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cd41cdd81397470ca76b05a2d12329df
Source dataset
uspto-grants-2013_07
Patent number
US08481502B2

Reaction notes

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