1,2-Dichloroethane → HCID 11432640, compound

HRID 2106437Notes

Reaction equation

HRID 2106437 reaction equation
[C:1]([C:5]1([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([C:23]3[O:24][C:25]4[CH:31]=[CH:30][C:29]([C:32](O)=[O:33])=[CH:28][C:26]=4[CH:27]=3)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:13]=2[CH3:35])[O:9][CH2:8][CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.Cl.C[O:42][C:43](=[O:46])[CH2:44][NH2:45]>CN(C1C=CN=CC=1)C>[C:1]([C:5]1([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([C:23]3[O:24][C:25]4[CH:31]=[CH:30][C:29]([C:32]([NH:45][CH2:44][C:43]([OH:46])=[O:42])=[O:33])=[CH:28][C:26]=4[CH:27]=3)([CH2:19][CH3:20])[CH2:21][CH3:22])=[CH:14][C:13]=2[CH3:35])[O:9][CH2:8][CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 122755Glycine methyl ester hydrochlorideHCID 11386089HCID 11386089, compound

Product 1

HCID 11432640HCID 11432640, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

2-{1-[4-(2-tert-butyl-[1,3]dioxolan-2-ylmethoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzofuran-5-carboxylic acid (125 mg, 0.260 mmol), EDC (75 mg, 0.391 mmol), DMAP (95 mg, 0.781 mmol), and glycine methyl ester hydrochloride (49 mg, 0.39 mmol) are reacted to produce the intermediate followed by hydrolysis analogous to Example 1, step K to give title compound (125 mg, 90%).

Workup

  1. customto produce the intermediate
  2. customfollowed by hydrolysis analogous to Example 1, step K

Sources & evidence

ORD record
ord-d56d78c4d96c494aac6c766c6a101768
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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