Methanol → HCID 131724076, compound

HRID 1168434Notes

Reaction equation

HRID 1168434 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@:14]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:15])[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][C:33](=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[O:11]C1OCC=C)(=[O:3])[CH3:2].N1(C2CCCCCCC2)CCC[CH2:46][CH2:45][CH2:44]N1.[CH3:58][OH:59]>>[CH2:46]([C:58]1([O:11][C@H:12]([CH2:31][O:32][C:33](=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@:14]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([OH:15])[C@H:5]1[NH:4][C:1](=[O:3])[CH3:2])[OH:59])[CH:45]=[CH2:44]

Participants

4

Reactant 3

HCID 887MethanolHCID 66583054DiazabicyclooctaneHCID 86584533HCID 86584533, compound

Product 1

HCID 131724076HCID 131724076, compound

Procedure

8 g of (f), 1.2 g of diazabicyclooctane (DABCO) and 3 g of tris triphenylphosphine rhodium chloride (Rh(PPh3)3Cl) in 400 ml of an aqueous methanol solution (90% v/v) were heated under reflux for 4 hours. After filtering through paper and concentrating, it was taken up in 250 ml of chloroform, washed with 5% (m/v) citric acid then with water. After drying and evaporating off the solvents, the crude mixture was taken up in 150 ml of an aqueous acetone solution (90%, m/v). 3 g of HgCl2 was added and it was stirred at ambient temperature for 60 minutes.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationAfter filtering through paper
  3. concentrationconcentrating
  4. washwashed with 5% (m/v) citric acid
  5. customAfter drying
  6. customevaporating off the solvents
  7. addition3 g of HgCl2 was added

Sources & evidence

ORD record
ord-c329aea24d5a4085adf5851c9c31f7dc
Source dataset
uspto-grants-2003_09
Patent number
US06624190B2

Reaction notes

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