Chloroiodomethane → 3,3-bis(N-CBz-L-valyloxymethyl)-propionic acid chloromethyl ester

HRID 989917Notes

Reaction equation

HRID 989917 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH:20]([CH2:25][O:26][C:27](=[O:43])[C@H:28]([CH:40]([CH3:42])[CH3:41])[NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:21][C:22]([OH:24])=[O:23])=[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].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:62][CH2:63]I>O1CCOCC1>[Cl:62][CH2:63][O:23][C:22](=[O:24])[CH2:21][CH:20]([CH2:25][O:26][C:27](=[O:43])[C@H:28]([CH:40]([CH3:42])[CH3:41])[NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:19][O:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 11644ChloroiodomethaneHCID 2723671Tetrabutylammonium HydroxideHCID 233875233,3-bis(N-CBz-L-valyloxymethyl)-propionic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,3-bis(N-CBz-L-valyloxymethyl)-propionic acid (3 g, 5 mmole) was dissolved in dioxane (20 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 3.11 ml, 4.8 mmole). The solution was dried in vacuo, and it was coevaporated with toluene several times. The residue was dissolved in methylene chloride (15 ml) and then chloroiodomethane (7.3 ml, 100 mmole) was added to the solution. The reaction solution was refluxed for 18 hr and then evaporated and the product was isolated with silica gel column chromatography. 900 mg.

Workup

  1. customThe solution was dried in vacuo, and it
  2. dissolutionThe residue was dissolved in methylene chloride (15 ml)
  3. temperatureThe reaction solution was refluxed for 18 hr
  4. customevaporated
  5. customthe product was isolated with silica gel column chromatography

Sources & evidence

ORD record
ord-69226d27e259469699ec1af60d7e90df
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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