L-Alaninol → HCID 178434994, compound

HRID 1695345Notes

Reaction equation

CO[C:3]([C:5]1[NH:6][N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:9]=1)=[O:4].C[O:25][C:26]([C:28]1[NH:29]N=C(OCC2C(C3C=CC=CC=3)=NOC=2C)[CH:32]=1)=O.N[C@H](CO)C>>[OH:25][CH2:26][C@@H:28]([NH:29][C:3]([C:5]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[NH:7][N:6]=1)=[O:4])[CH3:32]

Participants

Reactant 3

HCID 80307L-Alaninol

HCID 66643702HCID 66643702, compound

HCID 66643884HCID 66643884, compound

Product 1

HCID 178434994HCID 178434994, compoundYield 50%

Procedure

As described for example 6, 5-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester (70 mg, 0.22 mmol), instead of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester, was converted, using L-alaninol instead of ethanolamine, to the title compound (40 mg, 50%) which was obtained as a colorless oil. MS: m/e=358.2 [M+H]+.

Sources & evidence

ORD record: ord-6f6966511b594987a78bd3ca717eeb17
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163728B2

Reaction notes

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