Sodium Hydroxide → 3-Allyloxycarbonylamino-4-oxo-5-phenyl-pentanoic acid tert-butyl ester

HRID 722741Notes

Reaction equation

HRID 722741 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][CH:8]([NH:18][C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH:9]([OH:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.CCOCC>[C:1]([O:5][C:6](=[O:25])[CH2:7][CH:8]([NH:18][C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 235714393-Allyloxycarbonylamino-4-hydroxy-5-phenyl-pentanoic acid tert-butyl ester

Product 1

HCID 235714403-Allyloxycarbonylamino-4-oxo-5-phenyl-pentanoic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-allyloxycarbonylamino-4-hydroxy-5-phenyl-pentanoic acid tert-butyl ester, 107, (0.8 g, 2.23 mmol) in CH2Cl2 (10 mL) is added to a solution of Dess-Martin reagent (1.05 g, 2.47 mmol) in CH2Cl2 (10 mL). After 1 hour the reaction solution is diluted with ether (50 mL) and the solution poured into a 1.3 M solution of NaOH (20 mL). Stir for 1 hour and decant the organic layer. Dry the organic layer over Na2SO4, concentrate in vacuo to afford a crude residue that is purified over silica to afford the desired product.

Workup

  1. customdecant the organic layer
  2. dry with materialDry the organic layer over Na2SO4
  3. concentrationconcentrate in vacuo
  4. customto afford a crude residue that
  5. customis purified over silica

Sources & evidence

ORD record
ord-5ef5897ce7fb43538d30bb5b861a4e1b
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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