Sodium Thiosulfate → HCID 57562391, compound

HRID 1725334Notes

Reaction equation

HRID 1725334 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:31])[NH:7][C@H:8]([C:13]([NH:15][C@@H:16]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:17]([OH:23])[C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:31])[NH:7][C@H:8]([C:13]([NH:15][C@@H:16]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:17](=[O:23])[C:18](=[O:19])[NH:20][CH2:21][CH3:22])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68809848HCID 68809848, compound

Product 1

HCID 57562391HCID 57562391, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((1S)-1-((((1S)-1-benzyl-3-ethylamino-2-hydroxy-3-oxo-propyl)amino)carbonyl)-3-methylbutyl)carbamic acid 2-methoxyethyl ester (0.7 g, 1.6 mmol) in CH2Cl2 (70 mL) was added Dess-Martin periodinane (1.0 g, 2.4 mmol). The mixture was stirred at room temperature for 18 hours. Aqueous 10% Na2S2O3 (35 mL) and saturated aqueous NaHCO3 (35 mL) were added thereto, and the mixture was stirred at room temperature for 30 minutes. The organic layer was separated, washed with 1M HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl, dried over MgSO4, and concentrated in vacuo. The residue was crystallized from EtOAc/hexane to give the title compound (0.62 g, 88%) as colorless crystals. M.p. 138.0-138.3° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with 1M HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-6cb974b30d21477ca9ea732c0847378b
Source dataset
uspto-grants-2009_02
Patent number
US07491705B2

Reaction notes

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