Water → HCID 178501243, compound

HRID 2373699Notes

Reaction equation

HRID 2373699 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]([S:12](Cl)=[O:13])([CH3:11])[CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:28]1.O>O1CCCC1>[CH3:8][C:9]([S:12]([NH:26][C@H:27]1[CH2:28][CH2:29][C@H:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:31][CH2:32]1)=[O:13])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 46868612-Methylpropane-2-sulfinyl chlorideHCID 178501208HCID 178501208, compound

Product 1

HCID 178501243HCID 178501243, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1658 mL, 2.7 eq) was added dropwise to a solution of 2-methylpropane-2-sulfinyl chloride (3) (900 g, 1.3 eq) and methyl trans-4-amino-1-cyclohexane carboxylate p-toluenesulfonate (10) (1452 g, 4.407 mol) in tetrahydrofuran (9.5 L) with ice-cooling. The mixture was stirred for 1.5 hours at room temperature, poured into water (9.5 L) and extracted with ethyl acetate (9.5 L, 5 L). Each of organic layer was washed with brine twice, dried over sodium sulfate, and concentrated under reduced pressure to obtain (11) (1.26 kg).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (9.5 L, 5 L)
  3. washEach of organic layer was washed with brine twice
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2f436ecd21b4f928cd275fc63494050
Source dataset
uspto-grants-2008_12
Patent number
US07459580B2

Reaction notes

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