Dichloromethane → methyl 2-[N-(methoxycarbonylmethyl)amino]-3-(4-nitrophenyl)propionate

HRID 342839Notes

Reaction equation

HRID 342839 reaction equation
[NH2:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C(Cl)Cl.[K+].[Br-]>CO.C(Cl)Cl>[CH3:6][O:5][C:3]([CH2:2][NH:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4])=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 253877Potassium BromideHCID 560520Methyl 2-amino-3-(4-nitrophenyl)propanoate

Product 1

HCID 11055537methyl 2-[N-(methoxycarbonylmethyl)amino]-3-(4-nitrophenyl)propionateYield 36%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

This compound (7) was synthesized from compound 5 using a method analogous to the synthesis described in Example 4. FC (silica gel, first CH2Cl2, then 5% MeOH/CH2Cl2). Yield: 36%. IR (KBr): 3342 (N--H), 1740 (C=O), 1519,1347 (NO2), 1203 (C--O). 1N-NMR (CDCl3): 3.04 (dd, J=7.3, 13.7, 1H); 3.13 (dd, J=6.3, 13.7, 1H); 3.36 (d, J=17.3, 1H); 3.42 (d, J=17.3, 1H); 3.63 (dd, J=6.3, 7.3, 1H); 3.69 (s, 3H); 3.70 (s, 3H); 7.39 (d, J=8.8, 2H); 8.16 (d, J=8.8, 2H).

Sources & evidence

ORD record
ord-5aadcbb7ebc04f6a94f09d99c6cc5d9c
Source dataset
uspto-grants-1999_01
Patent number
US05859215

Reaction notes

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