Sodium Iodide → iodomethyl 5(N-CBz-L-valyloxy)-2,2-dimethylvalerate

HRID 1790766Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of chloromethyl 5-(N-CBz-L-valyloxy)-2,2-dimethylvalerate (3.85 g, 9 mmol) in acetonitrile (50 mL), was added sodium iodide (5.40 g, 36 mmol). 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 4.26 g of iodomethyl 5(N-CBz-L-valyloxy)-2,2-dimethylvalerate

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-f7023d254b9f4b65a57c2830ce8ec08f
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071173B2

Reaction notes

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