Water → HCID 66645054, compound

HRID 882851Notes

Reaction equation

HRID 882851 reaction equation
I(C1C=CC=CC=1C(O)=O)(=O)=O.[CH2:13]([N:20]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[NH:21][C:22](=[O:49])[CH:23]([OH:48])[CH:24]([NH:32][C:33]([C@H:35]1[CH2:39][CH2:38][C:37](=[O:40])[N:36]1[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:34])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+].O>CS(C)=O>[CH2:13]([N:20]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[NH:21][C:22](=[O:49])[C:23](=[O:48])[CH:24]([NH:32][C:33]([C@H:35]1[CH2:39][CH2:38][C:37](=[O:40])[N:36]1[CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:34])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1087942-Iodoxybenzoic acidHCID 516892Sodium BicarbonateHCID 66645016HCID 66645016, compound

Product 1

HCID 66645054HCID 66645054, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

IBX (189 mg, 0.303 mmol, 45 wt %) was added a solution of tert-butyl 1-benzyl-2-(3-((R)-1-benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoyl)-hydrazinecarboxylate (130 mg, 0.216 mmol) in DMSO (3 mL). After stiffing overnight saturated aqueous NaHCO3 solution (15 mL) and water (15 mL) were added. The mixture was extracted with EtOAc, the combined organic layers were washed with saturated aqueous NaHCO3 solution, water and dried (MgSO4). Purification by flash column chromatography (gradient 1-10% MeOH in DCM) provided the title compound (110 mg, 85%).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic layers were washed with saturated aqueous NaHCO3 solution, water
  3. dry with materialdried (MgSO4)
  4. customPurification by flash column chromatography (gradient 1-10% MeOH in DCM)

Sources & evidence

ORD record
ord-54c2495df3a04d08a9d6051b13a2b1e4
Source dataset
uspto-grants-2012_08
Patent number
US08236798B2

Reaction notes

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