Glycine ethyl ester, hydrochloride → HCID 57524617, compound

HRID 2278788Notes

Reaction equation

CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[CH:23]=3)[O:19][N:18]=2)=[CH:12][C:11]=1[CH2:35][CH3:36])(=O)=O.Cl.C([O:40][C:41](=[O:44])[CH2:42][NH2:43])C>>[CH:30]1([C:24]2[CH:23]=[C:22]([C:20]3[O:19][N:18]=[C:17]([C:13]4[CH:14]=[C:15]([CH3:16])[C:10]([O:9][CH2:8][CH2:7][CH2:6][NH:43][CH2:42][C:41]([OH:40])=[O:44])=[C:11]([CH2:35][CH3:36])[CH:12]=4)[N:21]=3)[CH:27]=[C:26]([O:28][CH3:29])[N:25]=2)[CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

Reactant 2

HCID 2723640Glycine ethyl ester, hydrochloride

HCID 86702021HCID 86702021, compound

Product 1

HCID 57524617HCID 57524617, compoundYield 41%

Procedure

The title compound (59 mg) is prepared as a pale yellow solid in analogy to the procedures given in Example 1 starting from 3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)propyl methanesulfonate (150 mg, 0.291 mmol) and glycine ethyl ester hydrochloride (203 mg, 1.46 mmol); LC-MS: tR=0.96 min, [M+H]+=495.25; 1H NMR (CD3OD): δ 7.88 (s, 1H), 7.86 (s, 1H), 7.53 (s, 1H), 7.28 (s, 1H), 3.98-4.03 (m, 2H), 4.00 (s, 3H), 3.84 (s, 2H), 3.38-3.44 (m, 2H), 3.24-3.31 (m, 1H), 2.78 (q, J=7.6 Hz, 2H), 2.41 (s, 3H), 2.23-2.32 (m, 2H), 2.06-2.17 (m, 2H), 1.85-1.97 (m, 4H), 1.72-1.82 (m, 2H), 1.32 (t, J=7.5 Hz, 3H).

Sources & evidence

ORD record: ord-d20abe8ec7184e2180af9199ef02d8af
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133179B2

Reaction notes

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