(4-Nitrophenyl)acetate → HCID 69532418, compound

HRID 1357462Notes

Reaction equation

HRID 1357462 reaction equation
[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:18]([NH:20][C@H:21]([C:23]([O:25][CH3:26])=[O:24])[CH3:22])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[N+](C1C=CC([CH2:36][C:37]([O-])=[O:38])=CC=1)([O-])=O>CN(C)C=O>[C:37]([NH:1][C@H:2]([C:11]([NH:13][C@H:14]([C:18]([NH:20][C@H:21]([C:23]([O:25][CH3:26])=[O:24])[CH3:22])=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)(=[O:38])[CH3:36]

Participants

4

Reactant 2

HCID 6931101(4-Nitrophenyl)acetateHCID 53888084HCID 53888084, compound

Product 1

HCID 69532418HCID 69532418, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.73 g (2.0 mmol) of methyl L-tyrosyl-L-valyl-L-alaninate (Example 1, Step A3) is dissolved in 5 ml of dimethylformamide, then 0.4 g (2.2 mmol) of p-nitro-phenyl-acetate is added. The reaction mixture is stirred at room temperature overnight then is evaporated at a pressure of 2.0-2.5 kPa. The residue is dissolved in 15 ml of ethyl acetate, the solution is washed with 3×5 ml of water, 5 ml of 1 M KHSO4 and 3×5 ml of water, then dried over anhydrous sodium sulfate and evaporated at a pressure of 2.0-2.5 kPa. The residue is rubbed with diethyl ether, filtered, washed with diethyl ether and dried in a vacuum desiccator.

Workup

  1. customthen is evaporated at a pressure of 2.0-2.5 kPa
  2. dissolutionThe residue is dissolved in 15 ml of ethyl acetate
  3. washthe solution is washed with 3×5 ml of water, 5 ml of 1 M KHSO4 and 3×5 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated at a pressure of 2.0-2.5 kPa
  6. filtrationfiltered
  7. washwashed with diethyl ether
  8. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-01ab3ac797454599b1497cef9c94fe16
Source dataset
uspto-grants-2003_07
Patent number
US06593300B1

Reaction notes

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