Water → HCID 86584533, compound

HRID 1168433Notes

Reaction equation

HRID 1168433 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][OH:32])[O:11][CH:6]1[O:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2].[C:33](Cl)(=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].O>C1(C)C=CC=CC=1>[C:1]([NH:4][C@@H:5]1[C@@:14]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([OH:15])[C@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=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][CH:6]1[O:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8124Octanoyl chlorideHCID 86584532HCID 86584532, compound

Product 1

HCID 86584533HCID 86584533, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
92.5 °C

Procedure

9.5 g of (e) and 5 g of octanoyl chloride in 150 ml of toluene was heated under reflux at 90-95° C. for 4 h. After cooling, the reaction mixture was poured into 600 ml of water and extracted with toluene. The organic phases were combined, washed with NaHCO3 then with water. Finally, after drying and evaporating off the solvents, the crude product was purified over silica to recover 8.6 g of (f) (Yield: 70%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with toluene
  3. washwashed with NaHCO3
  4. customFinally, after drying
  5. customevaporating off the solvents
  6. customthe crude product was purified over silica

Sources & evidence

ORD record
ord-102fa91cfbb94b939df8982dbc20f923
Source dataset
uspto-grants-2003_09
Patent number
US06624190B2

Reaction notes

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