Hydrochloric Acid → Methyl naphthalen-1-ylglycinate

HRID 1088586Notes

Reaction equation

HRID 1088586 reaction equation
C1([CH2:11][C:12]#[N:13])C2C(=CC=CC=2)C=CC=1.Cl.COC(=N)C[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.Cl[O-].[Na+].[CH3:33][O-:34].[Na+].C[OH:37]>>[CH3:33][O:34][C:11](=[O:37])[CH2:12][NH:13][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 887MethanolHCID 85961-NaphthaleneacetonitrileHCID 10942334Sodium MethoxideHCID 19863965Methyl 1-naphthaleneethanimidateHCID 23665760Sodium Hypochlorite

Product 1

HCID 10954942Methyl naphthalen-1-ylglycinate

Procedure

The N-3,5-dinitrobenzoyl-(R) or (S)-(α-naphthyl)-glycine of formula (III) may be prepared in a common method. For example, commercially available α-naphthylacetonitrile is treated with hydrogen chloride in methanol to thereby give methyl(α-naphthyl)acetoimidate. Then the resulting product is treated with sodium hypochlorite and sodium methylate to give (α-naphthyl)glycine methyl ester. Then this product is treated with 3,5-dinitrobenzoyl chloride. The N-3,5-dinitrobenzoyl-(RS)-(α-naphthyl)glycine methyl ester thus obtained is hydrolyzed to thereby give N-3,5-dinitrobenzoyl-(RS)-(α-naphthyl)glycine which is then optically resolved. Thus the aimed compound can be obtained.

Sources & evidence

ORD record
ord-788617cd386e4b1596a2d9630a4a676e
Source dataset
uspto-grants-1990_10
Patent number
US04963254

Reaction notes

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