Hydrochloric Acid → HCID 117812664, compound

HRID 591297Notes

Reaction equation

HRID 591297 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:10][C@H:11]([CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:37][CH2:38][F:39].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:10][C@H:11]([CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:37][CH2:38][F:39])=[CH:24][CH:23]=1)[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 70957077HCID 70957077, compound

Product 1

HCID 117812664HCID 117812664, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-[3-(4-hydroxyphenyl)propyl]-L-glutamate (80 mg, 0.16 mmol), 1-bromo-2-fluoroethane (103 mg, 0.81 mmol), and caesium carbonate (158 mg, 0.49 mmol) were dissolved in 8 ml N,N-dimethylformamide and the solution was stirred at 60° C. for 4 h. The reaction was then poured into 1 N aqueous hydrochloric acid (50 ml) and extracted with dichloromethane (3×75 ml). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by pHPLC 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. extractionextracted with dichloromethane (3×75 ml)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by pHPLC on a reversed phase (RP-18) column with an acetonitrile/water gradient
  5. customThe appropriate fractions were collected
  6. customthe acetonitrile evaporated under reduced pressure

Sources & evidence

ORD record
ord-0cae659ed2444c0899d166e0161e3717
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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