Glycine ethyl ester, hydrochloride → HCID 10830513, compound

HRID 2254684Notes

Reaction equation

HRID 2254684 reaction equation
[ClH:1].[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[C:9]([BH3-])#N.[Na+].Cl[C:14]1[C:15]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]([CH:19]=[CH:20][CH:21]=1)C=O>CO>[Cl:1][C:28]1[CH:29]=[C:24]([CH:25]=[CH:26][CH:27]=1)[CH2:23][O:22][C:15]1[CH:14]=[CH:21][C:20]([CH2:9][NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])=[CH:19][CH:16]=1

Participants

5

Reactant 3

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 54026983HCID 54026983, compound

Product 1

HCID 10830513HCID 10830513, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.07 g (0.066 mol) of glycine ethyl ester, hydrochloride are diluted in 200 ml of dry methanol and 3.32 g (0.053 mol) of sodium cyanoborohydride are added, while stirring under nitrogen. To this solution, 15 g (0.0608 mol) of 3-chlorobenzyloxybenzaldehyde are added in a single portion. Stirring is continued for 18 hours at room temperature, the mixture is evaporated to dryness and the crude residue chromatographed on silica gel (eluant: cyclohexane/ethyl acetate; 60/40). 6.8 g (34%) of [4-(3-chlorobenzyloxy)benzyl]amino acetic acid, ethyl ester are obtained (m.p. 114°-115° C. as hydrochloride). 3 g (0.0090 mol) of the above ester (free base) are heated in 70 ml of dimethylamine at 60° C. for 7 hours. The solution is allowed to stand overnight at room temperature, then evaporated and the residue is purified on silica gel (eluant: chloroform/methanol/30% NH4OH; 95/5/0.5) to afford 0.7 g (23%) of [4-(3-chlorobenzyloxy)benzyl]amino-N,N-dimethylacetamide, hydrochloride (m.p. 120°-125° C.). Analogously the following compounds can be obtained, starting from the corresponding ethyl esters:

Workup

  1. stirringStirring
  2. customthe mixture is evaporated to dryness
  3. customthe crude residue chromatographed on silica gel (eluant: cyclohexane/ethyl acetate; 60/40)

Sources & evidence

ORD record
ord-5d41066a9fe64829a740eceedac1fff7
Source dataset
uspto-grants-1993_08
Patent number
US05236957

Reaction notes

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