Glycine, N-methyl-, ethyl ester → HCID 86650566, compound

HRID 1746148Notes

Reaction equation

HRID 1746148 reaction equation
Br[C:2]1[CH2:6][CH2:5][O:4][N:3]=1.NC1CCON=1.C([O:15][C:16](=[O:20])[CH2:17][NH:18][CH3:19])C>>[O:4]1[CH2:5][CH2:6][C:2]([N:18]([CH3:19])[CH2:17][C:16]([OH:20])=[O:15])=[N:3]1

Participants

4

Reactant 3

HCID 95849Glycine, N-methyl-, ethyl esterHCID 1226904141832-92-2HCID 219834983-Bromo-4,5-dihydroisoxazole

Product 1

HCID 86650566HCID 86650566, compound

Procedure

2-((4,5-dihydroisoxazol-3-yl)(methyl)amino)acetic acid I-244a and I-244b were prepared in 2 steps according to the following procedure: racemic 3-bromo-4,5-dihydroisoxazole I-10 was converted to the corresponding 3-amino-4,5-dihydroisoxazole by reacting it with sarcosine ethyl ester under the same conditions as in Example 238. The ethyl ester was then hydrolyzed using the analogous conditions as in Example 119 to provide a mixture of racemic I-244. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M−H]−=327.5 m/z. Activity: B

Workup

  1. customto provide
  2. additiona mixture of racemic I-244
  3. customThese compounds can be separated

Sources & evidence

ORD record
ord-720be87f61ae411d956b5730c6ca5658
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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