Diisopropylethylamine → HCID 22644917, compound

HRID 2084879Notes

Reaction equation

HRID 2084879 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:11])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].C(N(CC)C(C)C)(C)C.[C:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)#[C:22][CH2:23][CH3:24]>C(Cl)Cl.C(#N)C>[CH2:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:11][C:6]2([C:4]([O:3][CH3:2])=[O:5])[CH2:10][CH2:9][CH2:8][CH2:7]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1)[C:22]#[C:23][CH3:24]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HClHCID 22644685HCID 22644685, compound

Product 1

HCID 22644917HCID 22644917, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of methyl-1-amino-1-cyclopentane carboxylate hydrochloride (15 g, 84.0 mmol) and N,N-diisopropylethylamine in methylene chloride (200 mL) and acetonitrile (50 mL), 4-butynyloxyphenylsulfonylchloride (24.7 g, 100 mmol) was slowly added at room temperature. 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. Chloroform layer was filtered and concentrated. The product was crystallized from a mixture acetone:hexane (1:1) to give methyl 1-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)cyclopentane carboxylate as white crystals, 26.8 g (91%), mp 81-3° C. Electrospray Mass Spec 352 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-20ea655236784a2899da08e4685ce933
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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