Hydrochloric Acid → 4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-{2-[4-(benzyloxycarbonylmethylcarbamoyl)phenyl]ethyl}benzofuran

HRID 230923Notes

Reaction equation

HRID 230923 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]([C:42](O)=[O:43])=[CH:38][CH:37]=3)=[CH:32][O:33][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2].Cl.[NH2:46][CH2:47][C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl>C(N(CC)CC)C>[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:37]=[CH:38][C:39]([C:42](=[O:43])[NH:46][CH2:47][C:48]([O:50][CH2:51][C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[O:49])=[CH:40][CH:41]=3)=[CH:32][O:33][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11701227Benzyl 2-aminoacetate hydrochlorideHCID 671358094-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[2-(4-carboxyphenyl)ethyl]benzofuran

Product 1

HCID 671359484-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-{2-[4-(benzyloxycarbonylmethylcarbamoyl)phenyl]ethyl}benzofuranYield 63.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[2-(4-carboxyphenyl)ethyl]benzofuran (0.12 g) in N,N-diemthylformamide (2 mL) were added benzyl 2-aminoacetate hydrochloride (48 mg), 1-hydroxybenzotriazole (32 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (77 mg) and triethylamine (0.11 mL), and the mixture was stirred at room temperature for three days. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1-1/2) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-{2-[4-(benzyloxycarbonylmethylcarbamoyl)phenyl]ethyl}benzofuran (94 mg). This material was dissolved in methanol (3 mL). To the solution was added 10% palladium-carbon powder (40 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 1 hour. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give the title compound (82 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1-1/2)

Sources & evidence

ORD record
ord-3480a75802764e67a0d691650e0fb7f4
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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