Tetraethylene Glycol → HCID 131721706, compound

HRID 378167Notes

Reaction equation

HRID 378167 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]([NH:21][C:22](=[O:40])[CH2:23][NH:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]3[NH:35][CH2:36][CH2:37][CH2:38][N:39]=3)[CH:28]=2)=[O:26])[CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[C:13]([Cl:15])[CH:14]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:53]([OH:65])[CH2:54][O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH2:62][CH2:63]O>CC(N(C)C)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]([NH:21][C:22](=[O:40])[CH2:23][NH:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]3[NH:39][CH2:38][CH2:37][CH2:36][N:35]=3)[CH:28]=2)=[O:26])[CH2:17][C:18]([O:20][CH2:63][CH2:62][O:61][CH2:60][CH2:59][O:58][CH2:57][CH2:56][O:55][CH2:54][CH2:53][OH:65])=[O:19])[CH:12]=[C:13]([Cl:15])[CH:14]=1

Participants

5

Reactant 3

HCID 8200Tetraethylene GlycolHCID 682631,1'-CarbonyldiimidazoleHCID 131721707HCID 131721707, compound

Product 1

HCID 131721706HCID 131721706, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To the product of Example 200 (200 mg, 0.00033 mole) in DMA (1.5 mL) was added carbonyldiimidazole (67 mg, 0.00041 mole). The reaction was stirred at room temperature for 1 hour. Tetraethyleneglycol (214 mg, 0.0011 mole) was then added and the reaction mixture was stirred overnight at 60° C. The reaction was cooled to room temperature and the product was isolated by RPHPLC to yield the title compound (120 mg after lyophilization) as a hygroscopic white solid. MS and NMR were consistent with the desired structure.

Workup

  1. stirringthe reaction mixture was stirred overnight at 60° C
  2. temperatureThe reaction was cooled to room temperature
  3. customthe product was isolated by RPHPLC

Sources & evidence

ORD record
ord-de7c38be6f3b4fe3896cbe3cf5f55ff8
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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