Sodium Iodide → HCID 23387576, compound

HRID 990020Notes

Reaction equation

HRID 990020 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH:20]([O:30][C:31](=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[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-:50].[Na+]>C(#N)C>[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH:20]([O:30][C:31](=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:21][C:22]([CH3:29])([CH3:28])[C:23]([O:25][CH2:26][I:50])=[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

4

Reactant 2

HCID 5238Sodium IodideHCID 23387571HCID 23387571, compound

Product 1

HCID 23387576HCID 23387576, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of chloromethyl 5-(N-CBz-L-valyloxy)-4-stearoyloxy-2,2-dimethylvalerate (7.8 g, 11 mmol) in acetonitrile (100 mL), was added sodium iodide (6.5 g, 44 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 7.84 g of iodomethyl 5-(N-CBz-L-valyloxy)-4-stearoyloxy-2,2-dimethylvalerate.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with aqueous sodium thiosulfate (0.1 M)
  5. customThe organic phase was dried (NA2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed (silica gel, 1%MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6e8ead00e4a44ca79eb92ff604d260f0
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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