HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Glycolic Acid | HCID 757 | — |
| Reactant | Rac-1-amino-3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-propan-2-ol | HCID 67265790 | — |
| Product | 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 | HCID 67265914 | 54.1% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08148410B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-40f3a00f75764805afa94b019241a7b1 |
| Source note | uspto-grants-2012_04 |