Sodium Iodide → HCID 10175121, compound
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]([CH2:32][CH3:33])[CH2:30][CH3:31])=[O:28].[I-].[Na+].[CH2:36]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH3:37].CN(C)C=[O:46]>>[CH2:30]([N:29]([CH2:32][CH3:33])[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][CH2:37][C:36](=[O:46])[N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])=[O:2])=[O:24])=[O:23])=[O:28])[CH3:31]Participants
6
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 137 ml (1 mmol) 2-chloro-N,N-diethylacetamide in 3 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. The organic extracts were dried with sodium sulfate and the solvent was distilled off to yield 260 mg (92%) of (R)-1-{6-[(R)-2-(diethylcarbamoyl-methoxycarbonyl)-pyrrolidin-1-yl]-6-oxo-hexanoyl}-pyrrolidine-2-carboxylic acid diethylcarbamoyl-methyl ester as a yellow oil, MS m/e (%): 567 (M+H+, 100).
Workup
- distillationwas distilled off
- extractionextracted with water
- dry with materialThe organic extracts were dried with sodium sulfate
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-3cd242875e324798acfaa863b852dedf
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06903129B2
Reaction notes
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