Idoxuridine → HCID 18667132, compound

HRID 1816511Notes

Reaction equation

HRID 1816511 reaction equation
[I:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.[C:18](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:19]1[CH:26]=[CH:25][C:22]([O:23][CH3:24])=[CH:21][CH:20]=1>N1C=CC=CC=1>[I:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][O:13][C:18]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:19]2[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[CH:25][CH:26]=2)[C@@H:9]([OH:10])[CH2:8]1

Participants

4

Reactant 2

HCID 5905IdoxuridineHCID 84462p-(Chlorodiphenylmethyl)anisole

Product 1

HCID 18667132HCID 18667132, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2 g of 5-iodo-2′-deoxyuridine (5.65 mmole) was dissolved in 30 ml of pyridine, 5 ml of TEA and 2.16 g of MMTr-Cl (6.99 mmole) were sequentially added thereto, and stirred at room temperature for 4 hours. Then, pyridine was removed under a reduced pressure with a rotary evaporator, the residue was treated with a mixture of water and CH2Cl2, the CH2Cl2 layer was separated, dried under MgSO4, and then, CH2Cl2 was removed under a reduced pressure. The resulting residue was subjected to column chromatography (silica gel 60, 230˜400 meshes, Merck) to obtain the title compound as a pale yellow solid. The chromatography was conducted using a mixture of CH2Cl2 and methanol as an eluting solution whose mix ratio was gradually changed from 100:1 to 50:1 (v/v).

Workup

  1. customThen, pyridine was removed under a reduced pressure with a rotary evaporator
  2. additionthe residue was treated with a mixture of water and CH2Cl2
  3. customthe CH2Cl2 layer was separated
  4. customdried under MgSO4
  5. customCH2Cl2 was removed under a reduced pressure

Sources & evidence

ORD record
ord-b736c9fb92144566a09a0ae4e567ec10
Source dataset
uspto-grants-2005_04
Patent number
US06884882B1

Reaction notes

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