Acetic Anhydride → HCID 10115492, compound

HRID 1072967Notes

Reaction equation

HRID 1072967 reaction equation
[OH:1][N:2]([CH2:6][CH2:7][CH2:8][O:9][CH2:10][N:11]1[C:18]([CH2:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)=[C:17]([CH:28]([CH3:30])[CH3:29])[C:15](=[O:16])[NH:14][C:12]1=[O:13])[C:3]([NH2:5])=[O:4].C(N(CC)CC)C.[C:38](OC(=O)C)(=[O:40])[CH3:39].[Na]>ClCCl.CN(C)C1C=CN=CC=1>[C:38]([O:1][N:2]([CH2:6][CH2:7][CH2:8][O:9][CH2:10][N:11]1[C:18]([CH2:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)=[C:17]([CH:28]([CH3:30])[CH3:29])[C:15](=[O:16])[NH:14][C:12]1=[O:13])[C:3]([NH2:5])=[O:4])(=[O:40])[CH3:39]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 5360545SodiumHCID 10295507HCID 10295507, compound

Product 1

HCID 10115492HCID 10115492, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 1-(3-N1-hydroxyureidopropyloxymethyl)-6-(3,5-dimethylbenzyl)-5-isopropyluracil obtained in the above Example 1-C (85 mg, 0.2 mmol) in dichloromethane (3.5 ml), was added DMAP (4-dimethylaminopyridine) (5 mg, 0.04 mmol), triethylamine (45 μl, 0.3 mmol) and acetic anhydride (25 μl, 0.24 mmol) and the mixture was stirred for 3 hours at 20° C. Then, it was added thereto dichloromethane (5 ml) and an aqueous saturated sodium hydrogenocarbonate solution (5 ml). The reaction medium was then extracted with dichloromethane (50 ml) and the organic phase was washed with water (10 ml) and then with a saturated sodium chloride solution (10 ml) and dried (sodium sulfate). The organic phase was then concentrated and subjected to a flash column chromatography on silica gel (dichloromethane/methanol 9:1) to give 70 mg (75%) of the desired 1-(3-N1-acetoxyureidopropyloxymethyl)-6-(3,5-dimethylbenzyl)-5-isopropyluracil in the form of a solid.

Workup

  1. additionThen, it was added
  2. extractionThe reaction medium was then extracted with dichloromethane (50 ml)
  3. washthe organic phase was washed with water (10 ml)
  4. dry with materialwith a saturated sodium chloride solution (10 ml) and dried (sodium sulfate)
  5. concentrationThe organic phase was then concentrated

Sources & evidence

ORD record
ord-4e59b5b5b8d94e9892f03ec7fc49b3d3
Source dataset
uspto-grants-2005_06
Patent number
US06911450B1

Reaction notes

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