Diisopropylethylamine → HCID 22644783, compound

HRID 2084875Notes

Reaction equation

HRID 2084875 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].C(N(CC)C(C)C)(C)C.[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)[C:23]#[C:24][CH3:25]>C(Cl)Cl.C(#N)C>[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:12][C:6]2([C:4]([O:3][CH3:2])=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)(=[O:35])=[O:34])=[CH:29][CH:28]=1)[C:23]#[C:24][CH3:25]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 22645079Methyl 1-aminocyclohexane-1-carboxylate hydrochloride

Product 1

HCID 22644783HCID 22644783, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of methyl-1-amino-1-cyclohexane carboxylate hydrochloride (10 g, 51.7 mmol) and N,N-diisopropylethylamine in methylene chloride (200 mL) and acetonitrile (50 mL), 4-but-2-ynyloxy-benzenesulfonyl chloride (14.0 g, 56.8 mmol) was slowly added at room temperature. The reaction mixture was stirred for 16 hrs and evaporated to dryness. It was extracted with chloroform, washed well with water and dried over anhydrous MgSO4. The chloroform layer was filtered and concentrated. The product was crystallized from a mixture acetone:hexane 1:10 to give methyl 1-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)cyclohexanecarboxylate as white crystals, 12.5 g.(66%), mp 118-2° C. Electrospray Mass Spec 366 (M+H)+.

Workup

  1. additionwas slowly added at room temperature
  2. customevaporated to dryness
  3. extractionIt was extracted with chloroform
  4. washwashed well with water
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationThe chloroform layer was filtered
  7. concentrationconcentrated
  8. customThe product was crystallized from a mixture acetone:hexane 1:10

Sources & evidence

ORD record
ord-a6ab09d257d842babd0b0436d38a4b03
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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