Methyl 3-allylamino-2-benzyloxycarbonylamino-2-methylpropionate → Methyl 3-amino-2-benzyloxycarbonylamino-2-methylpropionate

HRID 1994432Notes

Reaction equation

HRID 1994432 reaction equation
C([NH:4][CH2:5][C:6]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])([CH3:11])[C:7]([O:9][CH3:10])=[O:8])C=C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[NH2:4][CH2:5][C:6]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])([CH3:11])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 68691822Methyl 3-allylamino-2-benzyloxycarbonylamino-2-methylpropionate

Product 1

HCID 68692239Methyl 3-amino-2-benzyloxycarbonylamino-2-methylpropionateYield 83.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.22 g (1.42 mmol) of N,N-dimethylbarbituric acid, 0.02 g (0.017 mmol) of Pd(PPh3)4, 1.5 ml of DCM and 0.145 g (0.47 mmol) of methyl 3-allylamino-2-benzyloxycarbonylamino-2-methylpropionate is heated at 35° C. for 2 h. The reaction solution is subsequently concentrated in vacuo, and then 20 ml of diethyl ether are added, and the solution is washed 3 times with 20 ml of saturated Na2CO3 each time. A pH of 2 is adjusted by dropwise addition of 4N HCl. The aqueous phase is separated off and extracted with 2 ml of EtOAc, and the solvent is removed in vacuo. 0.105 g of the desired product are obtained. MW (calculated, monoisotopic)=266, measured value: (M+H)+ 267.

Workup

  1. concentrationThe reaction solution is subsequently concentrated in vacuo
  2. addition20 ml of diethyl ether are added
  3. washthe solution is washed 3 times with 20 ml of saturated Na2CO3 each time
  4. additionA pH of 2 is adjusted by dropwise addition of 4N HCl
  5. customThe aqueous phase is separated off
  6. extractionextracted with 2 ml of EtOAc
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-20e83a8ebfc3406f8c36920650cb261d
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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