Sodium Iodide → HCID 53795415, compound

HRID 989987Notes

Reaction equation

Cl[CH2:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][O:15][C:16](=[O:32])[C@H:17]([CH:29]([CH3:31])[CH3:30])[NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:7]=1)=[O:5].[I-:33].[Na+]>C(#N)C>[I:33][CH2:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][O:15][C:16](=[O:32])[C@H:17]([CH:29]([CH3:31])[CH3:30])[NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:7]=1)=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-N-CBz-L-valyloxyethyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid chloromethyl ester (1.80 g, 3.87 mmol) in acetonitrile (30 mL), was added sodium iodide (2.32 g, 15.5mmol). The solution was stirred for 4 h at 60° C. The resulting suspension was filtered and the filtrate was evaporated. The residue was dissolved in CH2Cl2 and washed with aqueous sodium thiosulfate (0.1 M). The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The crude product was column chromatographed (silica gel, 1% MeOH in CH2Cl2), to give 2.04 g 1-(2-N-CBz-L-valyloxyethyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid iodomethyl ester.

Workup

filtrationThe resulting suspension was filtered
customthe filtrate was evaporated
dissolutionThe residue was dissolved in CH2Cl2
washwashed with aqueous sodium thiosulfate (0.1 M)
dry with materialThe organic phase was dried (Na2SO4)
concentrationconcentrated under reduced pressure
customchromatographed (silica gel, 1% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-7d4ff5d14a614cf4b6a5d24ea43404ec
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06458772B1

Reaction notes

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