Diisopropylethylamine → HCID 22644783, compound

HRID 2414582Notes

Reaction equation

HRID 2414582 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-9043450bca9b47978d311d5527cfa76f
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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