1,2-Dimethoxyethane → HCID 67197684, compound

HRID 544893Notes

Reaction equation

HRID 544893 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:34]=[O:35])=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]1[O:13][C:14](=[O:16])[CH3:15].[F:36][CH:37]([F:48])[O:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.COCCOC>O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:34]([C:42]1[CH:43]=[CH:44][C:39]([O:38][CH:37]([F:48])[F:36])=[CH:40][CH:41]=1)[OH:35])=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]1[O:13][C:14](=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 230821464-(Difluoromethoxy)benzeneboronic acidHCID 866202484-Chloro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-indole-3-carboxaldehyde

Product 1

HCID 67197684HCID 67197684, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture solution of 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carboxaldehyde (50 mg) obtained in Example 29-(1), 4-(difluoromethoxy)benzeneboronic acid (55 mg), hydroxyl(1,5-cyclooctadiene)rhodium(I) dimer (1.3 mg) and tri-tert-butylphosphine (0.6 mg) in H2O (1.0 ml)-1,2-dimethoxy-ethane (2.0 ml) was stirred at 80° C. under argon atmosphere for 19 hours. The reaction mixture was cooled to room temperature, and extracted with ethyl acetate (20 ml). The organic layer was filtered through an aminosilane-treated silica gel pad, and the filtrate was evaporated under reduced pressure to give crude 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indol-3-yl 4-(difluoromethoxy)phenyl methanol, which was used in the subsequent step without further purification.

Workup

  1. extractionextracted with ethyl acetate (20 ml)
  2. filtrationThe organic layer was filtered through an aminosilane-
  3. additiontreated silica gel pad
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-696e4e697b4d4432abe92746b402a676
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

Loading…