Glycine methyl ester hydrochloride → HCID 10323260, compound

HRID 1819930Notes

Reaction equation

HRID 1819930 reaction equation
[CH2:1]([C:3]([C:21]1[S:25][C:24]([C:26]([OH:28])=O)=[C:23]([CH3:29])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([CH2:18][CH3:19])([OH:17])[CH2:15][CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].Cl.[CH3:31][O:32][C:33](=[O:36])[CH2:34][NH2:35]>CN(C=O)C>[CH3:31][O:32][C:33](=[O:36])[CH2:34][NH:35][C:26]([C:24]1[S:25][C:21]([C:3]([CH2:1][CH3:2])([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([CH2:18][CH3:19])([OH:17])[CH2:15][CH3:16])=[C:8]([CH3:20])[CH:7]=2)[CH2:4][CH3:5])=[CH:22][C:23]=1[CH3:29])=[O:28]

Participants

4

Reactant 2

HCID 122755Glycine methyl ester hydrochlorideHCID 10387315HCID 10387315, compound

Product 1

HCID 10323260HCID 10323260, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a procedure analogous to Example 38, 5-{1-Ethyl-1-[4-(2-ethyl-2-hydroxy-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-carboxylic acid (Example 51) (0.3 g, 0.72 mmol), glycine methyl ester hydrochloride, and DMF (2 mL) as reaction solvent to give the title compound (0.34 g, 0.69 mmol, 97%). 1H NMR (CDC3), δ 0.71 (t, J=7.1 Hz, 6H), 0.95 (t, J=7.1 Hz, 6H), 1.63-1.72 (m, 4H), 2.04-2.14 (m, 4H), 2.21 (s, 3H), 2.48 (s, 3H), 3.78 (s, 3H), 3.81 (s, 3H), 4.15 (d, J=5.2 Hz, 2H), 6.20 (t, J=5.2 Hz, 1H), 6.63 (s, 1H), 6.72 (d, J=8.4 Hz, 1H), 6.98-7.01 (m, 1H), 7.01-7.06 (m, 1H). LC/MS (m/z): calcd. for C27H38NO5S (M−H)−: 488.7; found: 488.5.

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-0d62eeac7c73427fbcef36dd147d9186
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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