Proton sponge → HCID 86754580, compound

HRID 1738592Notes

Reaction equation

HRID 1738592 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]([CH3:15])[CH3:14])[CH:6]=[CH:5][CH:4]=1.[F:17][B-:18]([F:21])([F:20])[F:19].[CH3:22][O+:23]([CH3:25])[CH3:24].CC1[C@@H](O)C[C@]2(O)C(C)(C)C=1[C@@H](O)C([C@@]1(C)[C@H]([C@@H]2OC(C2C=CC=CC=2)=O)[C@]2(OC(C)=O)CO[C@@H]2C[C@@H]1O)=O>ClCCl>[F:17][B-:18]([F:21])([F:20])[F:19].[CH3:22][O+:23]([CH3:25])[CH3:24].[CH3:14][N:13]([CH3:15])[C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[N:2]([CH3:16])[CH3:1])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 15427210-deacetylbaccatin IIIHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)

Product 1

HCID 86754580HCID 86754580, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,8-bis(dimethylamino)naphthalene (514 mg, 2.4 mmol, 12 equiv.), 4 Å molecular sieves (700 mg) and trimethyloxonium tetrafluoroborate (296 mg, 2 mmol, 10 equiv.) are successively added to a suspension of 10-deacetylbaccatin III (109 mg, 0.2 mmol) in dichloromethane (4 ml) at 25° C. After stirring for 24 h at room temperature, HPLC analysis indicates that the reaction mixture contains 7,10-dimethoxy-10-deacetylbaccatin in an assayed yield of 17%.

Sources & evidence

ORD record
ord-87e8db363849435299858140e981713c
Source dataset
uspto-grants-1999_10
Patent number
US05962705

Reaction notes

Loading…