Benzyl 2-aminoacetate hydrochloride → 4-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[2-(4-(2-[1-carboxy-1-(methyl)ethylcarbamoyl]ethyl)phenyl)ethyl]-benzofuran

HRID 230926Notes

Reaction equation

HRID 230926 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[C:30]2[C:31]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39](CCC(O)=O)=[CH:38][CH:37]=3)=[CH:32][O:33][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2].Cl.[NH2:48][C:49]([CH3:61])([CH3:60])[C:50]([O:52]CC1C=CC=CC=1)=[O:51].Cl.NCC([O:67][CH2:68][C:69]1C=CC=C[CH:70]=1)=O>>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[C:30]2[C:31]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([CH2:70][CH2:69][C:68](=[O:67])[NH:48][C:49]([C:50]([OH:52])=[O:51])([CH3:60])[CH3:61])=[CH:38][CH:37]=3)=[CH:32][O:33][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 11701227Benzyl 2-aminoacetate hydrochlorideHCID 21415531Benzyl 2-amino-2-methylpropanoate hydrochlorideHCID 671360804-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-{2-[4-(2-carboxyethyl)phenyl]ethyl}benzofuran

Product 1

HCID 671358204-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[2-(4-(2-[1-carboxy-1-(methyl)ethylcarbamoyl]ethyl)phenyl)ethyl]-benzofuran

Procedure

The title compound was prepared in a similar manner to that described in Example 84 using 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-{2-[4-(2-carboxyethyl)phenyl]ethyl}benzofuran and benzyl 2-amino-2-methylpropionate hydrochloride instead of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[2-(4-carboxyphenyl)ethyl]benzofuran and benzyl 2-aminoacetate hydrochloride, respectively.

Sources & evidence

ORD record
ord-927103ee21e943099b81ccaf457821df
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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