Glycine ethyl ester, hydrochloride → HCID 18363033, compound

HRID 2289274Notes

Reaction equation

HRID 2289274 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:10]=1[C:11]([NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12].NC1C=CC(C(N[C@H](C(OCC)=O)CCC(OCC)=O)=O)=C(F)C=1.Cl.C(OC(=O)CN)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(OCC)(=O)C.C(Cl)Cl>[F:8][C:9]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:10]=1[C:11]([NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12]

Participants

7

Reactant 4

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13691227HCID 13691227, compoundHCID 18363032HCID 18363032, compound

Product 1

HCID 18363033HCID 18363033, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Ethyl N-(2-fluoro-4-nitrobenzoyl)glycinate triethylamine (0.85 ml, 6.1 mmol) was added to a solution of 2-fluoro-4-nitrobenzoic acid (T. R. Jones et al., UK Patent GB 2175 903A, 1986) (1.0 g, 5.4 mmol), glycine ethyl ester hydrochloride (0.85 g, 6.1 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.1 g, 5.7 mmol) in methylene chloride (30 ml). After stirring 1 hour at room temperature the solution was passed through a short pad of silica gel eluting with ethyl acetate: methylene chloride (1:3) and the resulting white solid was filtered from hexane and dried under high vacuum to give ethyl N-(2-fluoro-4-nitrobenzoyl)glycinate (1.04 g). 1H NMR (DMSO-d6, 300 MHz) δ: 1.22 (t, J=7 Hz, 3H, CH3), 4.05 (d, J=6 Hz, 2H, glyCH2), 4.15 (q, J=7 Hz, 2H, ester CH2), 7.88 (t, J=8 Hz, 1H, Ar), 8.17 (dd, J=8.5, 1.5 Hz, 1H, Ar), 8.25 (dd, J=10, 2 Hz, 1H), 9.09 (br t, J=5.5 Hz, 1H, CONH). Anal. Calculated for C1H11FN2O5 : C, 48.89; H, 4.10; N, 10.37. Found: C, 49.00; H, 4.11; N, 10.43.

Workup

  1. filtrationthe resulting white solid was filtered from hexane
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-f563fddef77147769a1d0c25bec4ea70
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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