Sodium Thiosulfate → HCID 57562391, compound

HRID 2206350Notes

Reaction equation

HRID 2206350 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][CH2:25][CH2:26][O:27][C:28](=[O:53])[NH:29][C@H:30]([C:35]([NH:37][C@@H:38]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH:39]([OH:45])[C:40]([NH:42][CH2:43][CH3:44])=[O:41])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH3:23][O:24][CH2:25][CH2:26][O:27][C:28](=[O:53])[NH:29][C@H:30]([C:35]([NH:37][C@@H:38]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:39](=[O:45])[C:40](=[O:41])[NH:42][CH2:43][CH3:44])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33]

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

Triethylamine (1.1 g, 11 mmol) was added to a solution of the compound of Reference Example 1 (1.2 g, 3.6 mmol) and the compound of Reference Example 8 (1.0 g, 4.0 mmol) in DMF. This solution was stirred at room temperature for 18 hours and concentrated in vacuo. The residue was dissolved in ethyl acetate, and the solution was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated saline solution, dehydrated with anhydrous magnesium sulfate, and concentrated in vacuo. The resulting solid was washed with a liquid mixture of ethyl acetate/hexane (1:9) to yield ((1S)-1-((((1S)-1-benzyl-3-ethylamino-2-hydroxy-3-oxopropyl)amino)carbonyl)-3-methylbutyl)carbamic acid 2-methoxyethyl ester (0.75 g, 47%) as a white solid. A Dess-Martin reagent (1.0 g, 2.4 mmol) was added to a solution of ((1S)-1-((((1S)-1-benzyl-3-ethylamino-2-hydroxy-3-oxopropyl)amino)carbonyl)-3-methylbutyl)carbamic acid 2-methoxyethyl ester (0.7 g, 1.6 mmol) in dichloromethane (70 mL), and the resulting solution was stirred at room temperature for 18 hours. Thereafter, a 10% aqueous sodium thiosulfate solution (35 mL) and a saturated aqueous sodium hydrogen carbonate solution (35 mL) were added thereto, and the mixture was stirred at room temperature for 30 minutes. The organic layer was separated, washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated saline solution, dehydrated with anhydrous magnesium sulfate, and concentrated in vacuo. The residue was crystallized from a liquid mixture of ethyl acetate/hexane to yield the title compound (0.62 g, 88%) as a colorless crystal.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated saline solution
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from a liquid mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-8e9919c5e1d04b18999ebf9191d7fe0f
Source dataset
uspto-grants-2016_06
Patent number
US09371359B2

Reaction notes

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