1,2-Dichloroethane → HCID 11225963, compound

HRID 730978Notes

Reaction equation

HRID 730978 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:28]=[CH:27][C:20]3[S:21][C:22]([C:24](O)=[O:25])=[CH:23][C:19]=3[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29].C(Cl)CCl.Cl.C[O:39][C:40](=[O:43])[CH2:41][NH2:42]>CN(C1C=CN=CC=1)C>[CH3:32][C:2]([CH3:1])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:28]=[CH:27][C:20]3[S:21][C:22]([C:24]([NH:42][CH2:41][C:40]([OH:39])=[O:43])=[O:25])=[CH:23][C:19]=3[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 122755Glycine methyl ester hydrochlorideHCID 11374405HCID 11374405, compound

Product 1

HCID 11225963HCID 11225963, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

5-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzo[b]thiophene-2-carboxylic acid (310 mg, 0.686 mmol), DMAP (167 mg, 1.37 mmol), EDC (197 mg, 1.03 mmol), and glycine methyl ester hydrochloride (172 mg, 1.37 mmol) are reacted and hydrolyzed in a sequence analogous to Example 5 to afford the title compound (150 mg, 43%).

Sources & evidence

ORD record
ord-cef8593819c34e80865fa16f7950ce7b
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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