Methanol → HCID 11307151, compound

HRID 412855Notes

Reaction equation

HRID 412855 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:8]([O:15][C@@H:16]1[C@@H:29]([OH:30])[C@@H:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:27]([CH2:39][OH:40])[O:26][C@H:17]1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CO>N1C=CC=CC=1>[CH2:8]([O:15][C@@H:16]1[C@@H:29]([OH:30])[C@@H:28]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C@@H:27]([CH2:39][O:40][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[O:26][C@H:17]1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 62493Pivaloyl chlorideHCID 14332264HCID 14332264, compound

Product 1

HCID 11307151HCID 11307151, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under nitrogen gas atmosphere, pivaloyl chloride (4.2 ml, 35.7 mmol) was added to a solution of Compound 13 (7.3 g, 16.2 mmol) in pyridine (50 ml) at 0° C., and the mixture was stirred for 70 minutes. Methanol was added to the reaction mixture, and the mixture was stirred for 40 minutes, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1) to obtain Compound 14 (7.81 g, 90%).

Workup

  1. stirringthe mixture was stirred for 40 minutes
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-522738da94b843f29b6bb8089ac918fc
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

Loading…