Sodium Iodide → HCID 69463310, compound

HRID 1070893Notes

Reaction equation

HRID 1070893 reaction equation
[C:1]([C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:24])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@@H:17]1[C:21]([OH:23])=[O:22])=[O:15])([OH:3])=[O:2].Cl[CH2:26][C:27]([NH2:29])=[O:28].[I-].[Na+].[CH2:32]([N:34](CC)CC)[CH3:33].CN(C)C=[O:42]>>[C:27]([CH2:26][O:22][C:21]([C@H:17]1[CH2:18][CH2:19][CH2:20][N:16]1[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@@H:4]1[C:1]([O:3][CH2:33][C:32](=[O:42])[NH2:34])=[O:2])=[O:24])=[O:23])(=[O:28])[NH2:29]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 6580ChloroacetamideHCID 8471TriethylamineHCID 125516Miridesap

Product 1

HCID 69463310HCID 69463310, compoundYield 44%

Conditions

Temperature
90 °C

Procedure

To a solution of 170 mg (0.5 mmol) (R)-1-[6-[(R)-2-carboxy-pyrrolidin-1-yl]-6-oxo-hexanoyl]-pyrrolidine-2-carboxylic acid and 93.5 mg (1 mmol) 2-chloroacetamide in 2 ml dimethylformamide were added 14.9 mg (0.1 mmol) sodium iodide and 139 ml (1 mmol) triethylamine. After stirring overnight at 90° C. the solvent was distilled off, the residue was taken up with dichloromethane and extracted with water, 2% aqueous sodium bicarbonate and brine. The organic extracts were dried with sodium sulfate and the solvent was distilled off to yield 100 mg (44%) of (R)-1-[6-[(R)-2-carbamoylmethoxycarbonyl-pyrrolidin-1-yl]-6-oxo-hexanoyl]-pyrrolidine-2-carboxylic acid carbamoylmethyl ester as a light yellow foam, MS m/e (%): 455 (M+H+, 100).

Workup

  1. distillationwas distilled off
  2. extractionextracted with water, 2% aqueous sodium bicarbonate and brine
  3. dry with materialThe organic extracts were dried with sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-d277fe95fd504e0987b515b384137b10
Source dataset
uspto-grants-2005_06
Patent number
US06903129B2

Reaction notes

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