tert-Butanol → HCID 13755869, compound

HRID 2414043Notes

Reaction equation

HRID 2414043 reaction equation
C(O)(C)(C)C.[OH:6][CH2:7][CH:8]([S:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[C@@H:9]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CCOCC.ClCCl>[O:6]=[CH:7][CH:8]([S:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[C@@H:9]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 13755863HCID 13755863, compound

Product 1

HCID 13755869HCID 13755869, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of t-butanol (167 mg, 1.05 eq), 1,1,1-triacetoxy-2,1-benoxiodol-3(3H)-one (954 mg, 1.05 eq) and dry methylene chloride (8 ml) was stirred under argon at room temperature for 15 minutes. The mixture was then treated with a solution of (1S)-[3-hydroxy-2-[[(4-methoxyphenyl)methyl]thio]-1-(phenylmethyl)propyl]carbamic acid, 1,1-dimethylethyl ester (890 mg, 2.14 mmol) and dichloromethane (8 ml). After stirring for 15 minutes, the reaction was diluted with ether and poured into 1N sodium bicarbonate containing a seven-fold excess of sodium thiosulfate (3.9 g, 15.75 mmol). The mixture was stirred until all solids dissolved. The layers were separated and the organic phase washed with 1N sodium bicarbonate, water and brine. Drying over anhydrous magnesium sulfate and removal of solvent yielded the title compound as a pale yellow solid: 860 mg (2.08 mmol); Rf =0.75 (silica gel, benzene: ethyl acetate, 4:1).

Workup

  1. stirringAfter stirring for 15 minutes
  2. stirringThe mixture was stirred until all solids
  3. dissolutiondissolved
  4. customThe layers were separated
  5. washthe organic phase washed with 1N sodium bicarbonate, water and brine
  6. dry with materialDrying over anhydrous magnesium sulfate and removal of solvent

Sources & evidence

ORD record
ord-dd952a6350b548c0961f423ab1d3e4c2
Source dataset
uspto-grants-1988_01
Patent number
US04720585

Reaction notes

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