Sodium Iodide → HCID 53656531, compound

HRID 1078621Notes

Reaction equation

HRID 1078621 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]([OH:33])=[O:32])[C:26](=[O:34])[C@@H:25]1[CH2:35][C:36]([O:38][CH3:39])=[O:37])=[O:23])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].[CH3:42][N:43]([C:45]([CH2:47]Cl)=[O:46])[CH3:44].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[CH3:42][N:43]([CH3:44])[C:45]([CH2:47][O:32][C:31](=[O:33])[CH2:30][N:27]1[CH2:28][CH2:29][N:24]([C:22](=[O:23])[C@H:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[C@@H:25]([CH2:35][C:36]([O:38][CH3:39])=[O:37])[C:26]1=[O:34])=[O:46]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamideHCID 53836446HCID 53836446, compound

Product 1

HCID 53656531HCID 53656531, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 7.39 ml of N,N-dimethylformamide were dissolved 2.0 g of (S)-4-(N-benzyloxycarbonyl-O-methyl-L-tyrosyl)-3-methoxycarbonylmethyl-2-oxopiperazine-1-acetic acid, 83,0 mg of sodium iodide and 563 μl of N,N-dimethylaminocarbonylmethyl chloride. To the solution was added 772 μl of triethylamine while stirring at room temperature. The mixture was stirred for 6 hours, to which was then added water. The mixture was shaken with ethyl acetate for extraction. The organic layer was concentrated under reduced pressure. The residue was purified by means of a silica gel chromatography (methylene chloride/methanol =13/1) to give 1.57 g (68.0%) of the title compound as a colorless oily product.

Workup

  1. stirringThe mixture was stirred for 6 hours, to which
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by means of a silica gel chromatography (methylene chloride/methanol =13/1)

Sources & evidence

ORD record
ord-34d04c7de4614c0180075cbf30725dc3
Source dataset
uspto-grants-1996_08
Patent number
US05550131

Reaction notes

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