Hydrochloric Acid → HCID 178521056, compound

HRID 1625748Notes

Reaction equation

HRID 1625748 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH2:31][C:32]2[S:33][C:34]([C:37]3[N:38]=[N:39][N:40](COCC4C=CC=CC=4)[N:41]=3)=[CH:35][CH:36]=2)[CH:25]=1)(=O)C.Cl>CO>[C@@H:6]1([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH2:31][C:32]3[S:33][C:34]([C:37]4[NH:38][N:39]=[N:40][N:41]=4)=[CH:35][CH:36]=3)[CH:25]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666070431-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-3-(5-(2-benzyloxymethyl-2H-tetrazol-5-yl)-2-thienylmethyl)-4-chlorobenzene

Product 1

HCID 178521056HCID 178521056, compoundYield 115.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-(5-(2-benzyloxymethyl-2H-tetrazol-5-yl)-2-thienylmethyl)-4-chlorobenzene (247 mg), 6M aqueous hydrochloric acid solution (2 ml) and methanol (20 ml) was refluxed overnight. The solvent was evaporated under reduced pressure and the residue was triturated with diethyl ether to give the desired 1-(β-D-glucopyranosyl)-4-chloro-3-(5-(1H-tetrazol-5-yl)-2-thienylmethyl)benzene (172 mg) as colorless powder. ESI-Mass m/Z 437/439 (M−H).

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-208fc0a954ae4cf99d873ef7f43f1114
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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