Water → HCID 68481631, compound

HRID 1515239Notes

Reaction equation

HRID 1515239 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][SH:10])=[CH:7][CH:6]=1.[CH2:13]([O:15][C:16](=[O:34])[C@H:17]([NH2:33])[CH2:18][CH:19]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:20]OS(C)(=O)=O)[CH3:14].O>CN(C)C=O>[CH2:13]([O:15][C:16](=[O:34])[C@H:17]([NH2:33])[CH2:18][CH:19]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:20][S:10][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 86644348HCID 86644348, compound

Product 1

HCID 68481631HCID 68481631, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (5.5 g, 137.8 mmol) and 4-methoxybenzylmercaptan (15.4 mL, 110.2 mmol) were dissolved in N,N-dimethylformamide (150 mL), and the mixture was stirred for 10 min at 0°. To the resulting solution was added in drops (R)-4-BOC-amino-5-methanesulfonyloxy-pentanoic acid ethyl ester (46.7 g, 137.8 mmol) prepared in Step B, and the mixture was stirred for 4 h at 0°. Water was added thereto to quench the reaction, and the reaction mixture was extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound.

Workup

  1. stirringthe mixture was stirred for 4 h at 0°
  2. customto quench
  3. customthe reaction
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2fabe7a93cd844378a791f23addc4dc0
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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