Triacetoxyperiodinane → HCID 66644662, compound

HRID 882847Notes

Reaction equation

HRID 882847 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C@@H:5]([C:14]([OH:16])=O)[CH2:4][CH2:3]1.[NH2:17][CH:18]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:19]([OH:23])[C:20]([NH2:22])=[O:21].O[NH-].O=[N-].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[NH2:22][C:20](=[O:21])[C:19](=[O:23])[CH:18]([NH:17][C:14]([C@H:5]1[CH2:4][CH2:3][C:2](=[O:1])[N:6]1[CH2:7][C:8]1[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=1)=[O:16])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 5

HCID 159087TriacetoxyperiodinaneHCID 3001380Nitrate(1-), oxo-HCID 138823553-Amino-2-hydroxy-4-phenylbutanamideHCID 42127375HCID 42127375, compoundHCID 178514248HCID 178514248, compound

Product 1

HCID 66644662HCID 66644662, compound

Procedure

Coupling of (R)-5-oxo-1-pyridin-4-ylmethyl-pyrrolidine-2-carboxylic acid with 3-amino-2-hydroxy-4-phenylbutanamide and oxidation of the resulting hydroxyamide intermediate to the corresponding ketoamide using Dess Martin reagent.

Sources & evidence

ORD record
ord-eba976035cf342f7a9db16e4644a2ba1
Source dataset
uspto-grants-2012_08
Patent number
US08236798B2

Reaction notes

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