Iodine chloride → HCID 58868821, compound

HRID 1441964Notes

Reaction equation

HRID 1441964 reaction equation
[CH2:1]([O:8][C:9]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:10]=1[CH2:11][C@@H:12]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[I:41]Cl.S(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[C:34]([F:35])=[CH:33][C:32]([I:41])=[CH:31][C:10]=1[CH2:11][C@@H:12]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24640Iodine chlorideHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 58869031HCID 58869031, compound

Product 1

HCID 58868821HCID 58868821, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

12.5 g (26.1 mmol) of benzyl 2-(benzyloxy)-N-(tert-butoxycarbonyl)-3-fluoro-L-phenylalaninate are introduced into 200 ml of dichloromethane, and 8.76 g (104 mmol) of sodium bicarbonate are added. 8.46 g (52.4 mmol) of iodine monochloride in 10 ml of dichloromethane are slowly added dropwise. After 72 h, 300 ml of a 5% sodium bisulfite solution are added. The phases are separated and the organic phase is extracted with water. The organic phase is concentrated and the residue is purified on silica gel (cyclohexane:ethyl acetate 6:1).

Workup

  1. additionare added
  2. customThe phases are separated
  3. extractionthe organic phase is extracted with water
  4. concentrationThe organic phase is concentrated
  5. customthe residue is purified on silica gel (cyclohexane:ethyl acetate 6:1)

Sources & evidence

ORD record
ord-a426ff5b34564ff7945e7952ccdfe7c7
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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