Sodium Iodide → HCID 10152457, compound

HRID 1070894Notes

Reaction equation

HRID 1070894 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]([N:29]([CH3:31])[CH3:30])=[O:28].[I-].[Na+].[CH2:34]([N:36]([CH2:39]C)[CH2:37]C)[CH3:35].CN(C)C=[O:44]>>[CH3:30][N:29]([CH3:31])[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][CH2:35][C:34](=[O:44])[N:36]([CH3:39])[CH3:37])=[O:2])=[O:24])=[O:23])=[O:28]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamideHCID 125516Miridesap

Product 1

HCID 10152457HCID 10152457, compoundYield 84%

Conditions

Temperature
100 °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 103 ml (1 mmol) 2-chloro-N,N-dimethylacetamide in 2.5 ml dimethylformamide were added 14.9 mg (0.1 mmol) sodium iodide and 139 ml (1 mmol) triethylamine. After stirring overnight at 100° C. the solvent was distilled off, the residue was taken up with dichloromethane and extracted with water. The organic extracts were dried with sodium sulfite and the solvent was distilled off to yield 190 mg (84%) of (R)-1-{6-[(R)-2-(dimethylcarbamoyl-methoxycarbonyl)-pyrrolidin-1-yl]-6-oxo-hexanoyl}-pyrrolidine-2-carboxylic acid dimethylcarbamoyl-methyl ester as a yellow oil, MS m/e (%): 511 (M+H+, 100).

Workup

  1. distillationwas distilled off
  2. extractionextracted with water
  3. dry with materialThe organic extracts were dried with sodium sulfite
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-084f65d3401b45229f8ab3ac8fdc2848
Source dataset
uspto-grants-2005_06
Patent number
US06903129B2

Reaction notes

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