Sodium Iodide → 3,3-bis-(N-CBz-L-valyloxymethyl)propionic acid iodomethyl ester

HRID 989918Notes

Reaction equation

HRID 989918 reaction equation
Cl[CH2:2][O:3][C:4](=[O:45])[CH2:5][CH:6]([CH2:26][O:27][C:28](=[O:44])[C@H:29]([CH:41]([CH3:43])[CH3:42])[NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:7][O:8][C:9](=[O:25])[C@H:10]([CH:22]([CH3:24])[CH3:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[I-:46].[Na+]>C(#N)C>[I:46][CH2:2][O:3][C:4](=[O:45])[CH2:5][CH:6]([CH2:26][O:27][C:28](=[O:44])[C@H:29]([CH:41]([CH3:43])[CH3:42])[NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:7][O:8][C:9](=[O:25])[C@H:10]([CH:22]([CH3:24])[CH3:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 537927163,3-bis(N-CBz-L-valyloxymethyl)-propionic acid chloromethyl ester

Product 1

HCID 537890083,3-bis-(N-CBz-L-valyloxymethyl)propionic acid iodomethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,3-bis(N-CBz-L-valyloxymethyl)-propionic acid chloromethyl ester (900 mg, 1.38 mmole) was dissolved in acetonitrile (5 ml). Sodium iodide (289 mg, 1.93 mmole) was added to the solution. After reaction at 70° C. for 3 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (5 ml) and refiltered. The solution was dried and gave the titled product. 800 mg.

Workup

  1. customAfter reaction at 70° C. for 3 hr
  2. filtrationthe reaction mixture was filtered
  3. dissolutionthe residue was dissolved in methylene chloride (5 ml)
  4. customThe solution was dried

Sources & evidence

ORD record
ord-7299a55e3c704d389814f6144f409f98
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

Loading…