Water → HCID 14479244, compound

HRID 1200306Notes

Reaction equation

HRID 1200306 reaction equation
[CH3:1][O:2][C:3]1[CH:66]=[CH:65][C:6]([CH2:7][O:8][C:9]([C:11]2[N:12]3[C@H:15]([S:16][CH2:17][C:18]=2[CH2:19]Cl)[C@H:14]([NH:21][C:22](=[O:63])/[C:23](/[C:57]2[N:58]=[C:59]([NH2:62])[S:60][CH:61]=2)=[N:24]\[O:25][C@H:26]([C:41]([O:43][CH:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])[C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34](=[O:36])[CH3:35])=[C:29]([O:37][C:38](=[O:40])[CH3:39])[CH:28]=2)[C:13]3=[O:64])=[O:10])=[CH:5][CH:4]=1.[I-:67].[Na+].O>CC(C)=O>[CH3:1][O:2][C:3]1[CH:66]=[CH:65][C:6]([CH2:7][O:8][C:9]([C:11]2[N:12]3[C@H:15]([S:16][CH2:17][C:18]=2[CH2:19][I:67])[C@H:14]([NH:21][C:22](=[O:63])/[C:23](/[C:57]2[N:58]=[C:59]([NH2:62])[S:60][CH:61]=2)=[N:24]\[O:25][C@H:26]([C:41]([O:43][CH:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])[C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34](=[O:36])[CH3:35])=[C:29]([O:37][C:38](=[O:40])[CH3:39])[CH:28]=2)[C:13]3=[O:64])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 14479242HCID 14479242, compound

Product 1

HCID 14479244HCID 14479244, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the product obtained in Step 6 (14 g) in acetone (210 ml) was added sodium iodide (4.85 g) in total darkness and the mixture was stirred at room temperature for one hour. The reaction mixture was then poured into water (300 ml) and extracted twice with ethyl acetate (500 ml). The combined organic layer was washed with 5% sodium thiosulfate solution (200 ml) and brine (200 ml), and dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure, giving 15.1 g of the objective compound as yellow crystals.

Workup

  1. extractionextracted twice with ethyl acetate (500 ml)
  2. washThe combined organic layer was washed with 5% sodium thiosulfate solution (200 ml) and brine (200 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe dried solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b2092fd4e544bd49c19b9db18b4bd12
Source dataset
uspto-grants-1990_02
Patent number
US04904791

Reaction notes

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