Tributylphosphine → HCID 22644854, compound

HRID 1976472Notes

Reaction equation

HRID 1976472 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH:18]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]#[C:37][CH3:38])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])([S:14][CH2:15][CH2:16]O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH2:22]([O:21][C:19]([CH:18]1[C:11]2([CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]2)[S:14][CH2:15][CH2:16][N:24]1[S:25]([C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:35][C:36]#[C:37][CH3:38])=[CH:32][CH:33]=1)(=[O:26])=[O:27])=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 59756970HCID 59756970, compound

Product 1

HCID 22644854HCID 22644854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl {1-benzyl-4-[(2-hydroxyethyl)sulfanyl]-4-piperidinyl}({[4-(2-butynyloxy)phenyl]sulfonyl}amino)acetate (5.0 g, 8.9 mmol), tributylphosphine (4.04 g, 20 mmol) and 1,1-(azodicarbonyl)-dipiperidine (5.04 g, 20 mmol) was stirred in dry THF at room temperature for 6 h. The reaction sure was quenched with water, extracted with chloroform and washed well with water. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The product was purified by silica gel column chromatography eluting with 60% ethyl acetate/hexane to give ethyl-9-benzyl-4-{[4-(2-butynyloxy)phenyl]sulfonyl}-1-thia-4,9-diazaspiro[5.5]undecane-5-carboxylate as a pale yellow oil; Yield: 4.2 g (87.5%); Electrospray Mass Spec: 543 (M+H)+.

Workup

  1. customThe reaction
  2. customsure was quenched with water
  3. extractionextracted with chloroform
  4. washwashed well with water
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by silica gel column chromatography
  9. washeluting with 60% ethyl acetate/hexane

Sources & evidence

ORD record
ord-156a654cd79e4b2884b01933066f221d
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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