Sodium Iodide → HCID 23387397, compound

HRID 1170622Notes

Reaction equation

HRID 1170622 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][C:31]=1[O:32][C:33](=[O:49])[C@H:34]([CH:46]([CH3:48])[CH3:47])[NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[CH2:22][CH2:23][C:24]([O:26][CH2:27]Cl)=[O:25])=[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][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][C:31]=1[O:32][C:33](=[O:49])[C@H:34]([CH:46]([CH3:48])[CH3:47])[NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[CH2:22][CH2:23][C:24]([O:26][CH2:27][I:50])=[O:25])=[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 23387567HCID 23387567, compound

Product 1

HCID 23387397HCID 23387397, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

Chloromethyl 3,4-di-(N-CBZ-L-valyloxy)hydrocinnamate (1.9 g, 2.7 mmol) and sodium iodide (2 g, 13.3 mmol) were dissolved in acetonitrile (50 ml) and heated to 65° C. for 60 min. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane and filtrated. Removal of the solvent and purification by chromatography (ethyl acetate-hexane, 2:5) gave pure title product (1.9 g, 90%)

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationfiltrated
  3. customRemoval of the solvent and purification by chromatography (ethyl acetate-hexane, 2:5)

Sources & evidence

ORD record
ord-2e706c260c2a44668c3c82f236e935df
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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