1,2-Dichloroethane → HCID 11466349, compound

HRID 730970Notes

Reaction equation

HRID 730970 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[S:21][C:20]3[CH:22]=[C:23]([C:26](O)=[O:27])[CH:24]=[CH:25][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[S:21][C:20]3[CH:22]=[C:23]([C:26]([NH:42][CH2:41][C:40]([OH:39])=[O:43])=[O:27])[CH:24]=[CH:25][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 11224774HCID 11224774, compound

Product 1

HCID 11466349HCID 11466349, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

2-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzo[b]thiophene-6-carboxylic acid (175 mg, 0.387 mmol), DMAP (142 mg, 1.16 mmol), EDC (111 mg, 0.580 mmol), and glycine methyl ester hydrochloride (73 mg, 0.580 mmol) are reacted and hydrolyzed in a sequence analogous to Example 5 to afford the title compound (180 mg, 91%).

Sources & evidence

ORD record
ord-b1c68e8e8d8644a78592c4aaee76a962
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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