Triethylamine → HCID 13471176, compound

HRID 1815456Notes

Reaction equation

HRID 1815456 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[OH:19][C@@H:20]1[C:32]2[C:24](=[CH:25][C:26]3[O:30][CH2:29][O:28][C:27]=3[CH:31]=2)[C@@H:23]([C:33]2[CH:38]=[C:37]([O:39][CH3:40])[C:36]([OH:41])=[C:35]([O:42][CH3:43])[CH:34]=2)[C@@H:22]2[C:44](=[O:47])[O:45][CH2:46][C@@H:21]12>ClCCl>[C:9](=[O:10])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:41][C:36]1[C:35]([O:42][CH3:43])=[CH:34][C:33]([C@H:23]2[C@@H:22]3[C:44](=[O:47])[O:45][CH2:46][C@H:21]3[C@H:20]([OH:19])[C:32]3[C:24]2=[CH:25][C:26]2[O:30][CH2:29][O:28][C:27]=2[CH:31]=3)=[CH:38][C:37]=1[O:39][CH3:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 13337812HCID 13337812, compound

Product 1

HCID 13471176HCID 13471176, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.55 mmol of triethylamine and 0.37 mmol of benzyl chloroformate are added in succession to a solution of 0.25 mmol of (5R,5aS,8aS,9S)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one in 10 ml of anhydrous dichloromethane at 0° C. and under argon. After stirring for 1 hour, the reaction mixture is washed with water. The organic phase is then dried, filtered and subsequently concentrated under reduced pressure. Chromatography on silica gel (cyclohexane/ethyl acetate: 60/40) enables the expected product to be isolated.

Workup

  1. washthe reaction mixture is washed with water
  2. customThe organic phase is then dried
  3. filtrationfiltered
  4. concentrationsubsequently concentrated under reduced pressure
  5. customto be isolated

Sources & evidence

ORD record
ord-c148f5bd2d8c4c6abaa407abf5cea5f7
Source dataset
uspto-grants-2005_04
Patent number
US06878746B2

Reaction notes

Loading…