Ethanol → HCID 86725073, compound

HRID 1488236Notes

Reaction equation

HRID 1488236 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])=[O:17])[C:8](=[O:9])[C:7]2=[CH:26][CH:27]=1)([OH:3])=[O:2].[CH3:28][O:29][C:30]1[C:31]([O:50][CH3:51])=[C:32]([CH:47]=[CH:48][CH:49]=1)[C:33](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O)C>N1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:32]3[CH:47]=[CH:48][CH:49]=[C:30]([O:29][CH3:28])[C:31]=3[O:50][CH3:51])=[O:17])[C:8](=[O:9])[C:7]2=[CH:26][CH:27]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 66624882Dimethoxytrityl chloride2×HCID 86725074HCID 86725074, compound2×

Product 1

HCID 86725073HCID 86725073, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In an argon atmosphere, 1.02 g (2.70 mmol) of 1-[(4-carboxyphthalimidylethyl)aminocarbonyl]oxy-6-hexanol (compound 3a) was dissolved in 27 ml of pyridine. To the solution, 915 mg (2.70 mmol) of dimethoxytrityl chloride was added, and the mixture was stirred at room temperature. After 2 hours, 440 mg (1.30 mmol) of dimethoxytrityl chloride was further added to the reaction solution, and the mixture was stirred at room temperature for additional 2 hours. 5 ml of ethanol was added to the reaction solution, and the mixture was then concentrated under reduced pressure. The residue was dissolved in 150 ml of chloroform. The solution was washed with 50 ml of water twice and 50 ml of saturated saline once and dried over sodium sulfate. The solution was concentrated under reduced pressure, followed by azeotropy with 5 ml of toluene. The residue was purified by silica gel column chromatography (elution solvent: ethanol-chloroform, containing 0.3% pyridine) to obtain 1.88 g (pyridine salt, yield: 92%) of the title compound (compound 4a) as a yellow foam.

Workup

  1. stirringthe mixture was stirred at room temperature for additional 2 hours
  2. concentrationthe mixture was then concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 150 ml of chloroform
  4. washThe solution was washed with 50 ml of water twice
  5. dry with material50 ml of saturated saline once and dried over sodium sulfate
  6. concentrationThe solution was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent: ethanol-chloroform, containing 0.3% pyridine)

Sources & evidence

ORD record
ord-db0c29d1dd99483c95a3172772e0cb55
Source dataset
uspto-grants-2016_08
Patent number
US09428809B2

Reaction notes

Loading…