Sodium Hydroxide → Boc-Phe(3-CN)-OH

HRID 500979

Reaction equation

HRID 500979 reaction equation
[NH2:1][C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[N:11])[CH:5]=1.[OH-].[Na+].C(OC([O-])=O)(=O)[O:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O>O1CCOCC1>[NH:1]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[N:11])[CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 27345093-CyanophenylalanineHCID 86600350tert-Butoxycarbonyl dicarbonate

Product 1

HCID 2734498Boc-Phe(3-CN)-OH

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

2.5 g (13.1 mmol) of H-Phe(3-CN)—OH were dissolved in 100 ml of dioxane and, at 0° C., 13 ml (13 mmol) of 1N NaOH and 3.16 g (14.5 mmol) of Boc pyrocarbonate were added. The mixture was stirred at 0° C. for 20 min and then at room temperature for 4 h, during which a total of 7 ml (7 mmol) of 1N NaOH was added in portions, thus keeping the pH constant at 8-8.5. The solvent was removed in vacuo, and the residue was taken up in ethyl acetate, washed in each case 3× with 5% KHSO4 and 3× with NaCl-saturated water and then dried over Na2SO4. The solvent was removed in vacuo. A white solid was obtained as residue.

Workup

  1. waitat room temperature for 4 h
  2. customThe solvent was removed in vacuo
  3. washwashed in each case 3× with 5% KHSO4 and 3× with NaCl-saturated water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customA white solid was obtained as residue

Sources & evidence

ORD record
ord-9de363cdf8b84a26905c37569bf66bf3
Source dataset
uspto-grants-2010_08
Patent number
US07772251B2

Linked notes

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