Sodium Hydroxide → Bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)

HRID 976043Notes

Reaction equation

HRID 976043 reaction equation
C[C:2]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)([CH2:21][C:22]1[CH:27]=[CH:26][C:25]2[O:28][CH2:29][O:30][C:24]=2[CH:23]=1)[C:3]([NH:5][C@@:6]([CH3:20])([C:17]([OH:19])=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1.O.CCOCC>[CH2:39]1[O:38][C:35]2[CH:36]=[CH:37][C:32]([CH2:31][CH:2]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[C:3]([NH:5][C@@:6]([CH3:20])([C:17]([OH:19])=[O:18])[CH2:7][C:8]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:10][CH:9]=3)=[O:4])=[CH:33][C:34]=2[O:40]1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 86750507Methyl bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)

Product 1

HCID 86750508Bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)Yield 82.3%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.36 g (0.66 mmol) of methyl bis-(3,4-methylenedioxyphenylmethyl)acetyl-(α-methyl-D-tryptophan) in 10 mL MeOH and 2 mL THF was treated with a solution of 0.133 g (3.3 mmol) of NaOH in 2 mL H2O and the solution stirred at room temperature for 2 days. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed twice with 1N HCl, then saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure gave the product. This was dissolved in Et2O and the solvent removed under reduced pressure to give 0.28 g (82.3% yield) of the product as an amorphous white solid. The structure was confirmed by NMR and mass spectroscopy.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed twice with 1N HCl
  3. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  4. customgave the product
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3b4a85a92b9e4024a45c2487b4a94c20
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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