Glycolic Acid → Rac-n-(3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 1685772Notes

Reaction equation

[NH2:1][CH2:2][CH:3]([OH:28])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[S:17][C:18]([CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[C:19]([CH3:21])[CH:20]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1.[C:29](O)(=[O:32])[CH2:30][OH:31]>>[CH2:26]([N:23]([CH2:22][C:18]1[S:17][C:16]([C:14]2[O:13][N:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][CH:3]([OH:28])[CH2:2][NH:1][C:30](=[O:31])[CH2:29][OH:32])=[CH:6][CH:7]=3)[N:15]=2)=[CH:20][C:19]=1[CH3:21])[CH2:24][CH3:25])[CH3:27]

Participants

Reactant 2

HCID 757Glycolic Acid

HCID 67265790Rac-1-amino-3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-propan-2-ol

Product 1

HCID 67265914Rac-n-(3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-2-hydroxy-propyl)-2-hydroxy-acetamideYield 54.1%

Procedure

The title compound (31 mg) is prepared in analogy to Example 163 starting from rac-1-amino-3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-propan-2-ol (50 mg, 125 μmol) and glycolic acid (13 mg, 175 μmol); LC-MS: tR=0.68 min; [M+1]+=458.68. 1H NMR (CDCl3): δ1.09 (t, J=7.0 Hz, 6H), 2.23 (s, 3H), 2.62 (q, J=7.0 Hz, 4H), 2.75-2.87 (m, 2H), 3.18-3.28 (m, 1H), 3.50-3.58 (m, 1H), 3.70 (s, 2H), 3.94-4.02 (m, 1H), 4.06 (s, 2H), 7.14 (t, J=5.5 Hz, 1H), 7.33 (d, J=8.3 Hz, 2H), 7.64 (s, 1H), 8.03 (d, J=8.0 Hz, 2H).

Sources & evidence

ORD record: ord-40f3a00f75764805afa94b019241a7b1
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148410B2

Reaction notes

Loading…