Methyl 2-amino-2-ethylbutanoate → 2-(6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinamido)-2-ethylbutanoic acid

HRID 632267Notes

Reaction equation

HRID 632267 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:3][CH2:2]1.C[O:22][C:23](=[O:30])[C:24]([NH2:29])([CH2:27][CH3:28])[CH2:25][CH3:26]>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([NH:29][C:24]([CH2:27][CH3:28])([CH2:25][CH3:26])[C:23]([OH:30])=[O:22])=[O:14])[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 13412527Methyl 2-amino-2-ethylbutanoateHCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid

Product 1

HCID 710877392-(6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinamido)-2-ethylbutanoic acid

Procedure

The title compound can e.g. be synthesized by: i) coupling of 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 69 b) with 2-amino-2-ethyl-butyric acid methyl ester (CAN 70974-26-4) in analogy to Example 1; and ii) saponification of the ester group in analogy to the conditions described in Example 48 e), MS (EI): m/e=396.1 [M−H]−.

Sources & evidence

ORD record
ord-f57a440688af4d8497267d841949e6f5
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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