Sodium Hydroxide → HCID 68945227, compound

HRID 2189349Notes

Reaction equation

HRID 2189349 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]2[C:21](=[O:28])[NH:22][NH:23][C:24]=2[CH:25]([CH3:27])[CH3:26])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][C:30]([O:32][CH2:33][C@H:34]1[O:39][C@H:38](Br)[C@H:37]([O:41][C:42]([CH3:44])=[O:43])[C@@H:36]([O:45][C:46]([CH3:48])=[O:47])[C@@H:35]1[O:49][C:50]([CH3:52])=[O:51])=[O:31].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl>[C:42]([O:41][C@@H:37]1[C@@H:36]([O:45][C:46](=[O:47])[CH3:48])[C@H:35]([O:49][C:50](=[O:51])[CH3:52])[C@@H:34]([CH2:33][O:32][C:30](=[O:31])[CH3:29])[O:39][C@H:38]1[O:28][C:21]1[C:20]([CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:14][CH:15]=2)=[C:24]([CH:25]([CH3:26])[CH3:27])[NH:23][N:22]=1)(=[O:43])[CH3:44]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 68941151HCID 68941151, compound

Product 1

HCID 68945227HCID 68945227, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[4-(3-benzyloxypropoxy)phenyl]-methyl}-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (5.08 g), acetobromo-α-D-glucose (5.49 g) and benzyltri(n-butyl)ammonium chloride (2.08 g) in dichloromethane (40 mL) was added 5 mol/L aqueous sodium hydroxide solution (8 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=1/1-1/3-1/5). The purified material was further purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1-1/2-1/4) to give the title compound (2.75 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=1/1-1/3-1/5)
  2. customThe purified material was further purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1-1/2-1/4)

Sources & evidence

ORD record
ord-5f05de2305394f2c97c843176aba80bb
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

Loading…