Water → HCID 70674429, compound

HRID 591268Notes

Reaction equation

HRID 591268 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-:47].O>C(#N)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:10][CH:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][F:47])=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 28179Fluoride IonHCID 70674890HCID 70674890, compound

Product 1

HCID 70674429HCID 70674429, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propyl]benzyl}-L-glutamate (see Example 10) (100 mg, 0.15 mmol) was dissolved in 1 ml acetonitrile, and tetra-n-butylammonium tetra-(tert-butyl alcohol)-coordinated fluoride (Angew. Chem. 2008, 120, 8532-8534) (169 mg, 0.30 mmol) were added. The mixture was stirred at 70° C. for 2 h. Another 169 mg of the fluoride source was added and the reaction stirred for further 1.5 h at 70° C. After cooling to room temperature, the mixture was poured into water (10 ml) and extracted with tert-butyl methyl ether (3×10 ml). The organic phases were dried over magnesium sulfate and concentrated in vacuo. The residue was purified on a reversed phase (RP-18) column with an acetonitrile/water gradient. The appropriate fractions were collected, the acetonitrile evaporated under reduced pressure and the remaining aqueous solution was lyophilized.

Workup

  1. stirringthe reaction stirred for further 1.5 h at 70° C
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with tert-butyl methyl ether (3×10 ml)
  4. dry with materialThe organic phases were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a reversed phase (RP-18) column with an acetonitrile/water gradient
  7. customThe appropriate fractions were collected
  8. customthe acetonitrile evaporated under reduced pressure

Sources & evidence

ORD record
ord-30133387656a4bebb28672d0abf8cbac
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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