Ethanolamine → N-(2-hydroxyethyl)-2-[4-[(1R,3E)-3-hydroxyimino-1-(2-methylphenyl)-3-(2-methyl-4-pyridinyl)propyl]phenyl]acetamide

HRID 1617821Notes

Reaction equation

HRID 1617821 reaction equation
[OH:1]/[N:2]=[C:3](/[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=1)\[CH2:4][C@H:5]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](O)=[O:21])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].[NH2:30][CH2:31][CH2:32][OH:33].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O1CCCC1>[OH:33][CH2:32][CH2:31][NH:30][C:20](=[O:21])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:12])[CH2:4]/[C:3](=[N:2]\[OH:1])/[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1361668802-[4-[(1R,3E)-3-hydroxyimino-1-(2-methylphenyl)-3-(2-methyl-4-pyridinyl)propyl]phenyl]acetic acid

Product 1

HCID 136167082N-(2-hydroxyethyl)-2-[4-[(1R,3E)-3-hydroxyimino-1-(2-methylphenyl)-3-(2-methyl-4-pyridinyl)propyl]phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to example 207, step 2, {4-[(R)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-phenyl}-acetic acid (example 288) was coupled with 2-aminoethanol using benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate in tetrahydrofuran to give the title compound as a colourless oil, MS (ESI+): m/z=432.3 [M+H]+.

Sources & evidence

ORD record
ord-e2c09691d71143808201c29a4ae3ac13
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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