Sodium Azide → (-)-alpha-Amino-3-(azidomethyl)-4-hydroxybenzeneacetic acid

HRID 225311Notes

Reaction equation

HRID 225311 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:13]Cl)[CH:7]=1)[C:3]([OH:5])=[O:4].[N-:15]=[N+:16]=[N-:17].[Na+]>CO>[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:13][N:15]=[N+:16]=[N-:17])[CH:7]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 20296136(-)-alpha-Amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid

Product 1

HCID 23329747(-)-alpha-Amino-3-(azidomethyl)-4-hydroxybenzeneacetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (-)-α-amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid (252 mg, 1 mmole) in 4 ml of methyl alcohol is added sodium azide (156 mg, 2.4 mmole). The mixture is stirred at about 40° C. for 15 minutes. After about 10 minutes the title compound begins to precipitate. The mixture is cooled, filtered and the product is washed with a small amount of methyl alcohol and acetone. The title compound is collected (210 mg, 95% yield). M.P. >300°; [α]D18 =-73.03° (c 1.7, water), NMR (DMSO-D6) ppm (δ) 4.22 (s,1), 4.35 (s,2), 6.7-7.5 (superimposed q and s,3).

Sources & evidence

ORD record
ord-6a1c179e5ee54753b1a1a5eb5d33ae67
Source dataset
uspto-grants-1980_11
Patent number
US04236002

Reaction notes

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