Diisopropylethylamine → HCID 59756970, compound

HRID 1976471Notes

Reaction equation

HRID 1976471 reaction equation
[NH2:1][CH:2]([C:8]1([S:21][CH2:22][CH2:23][OH:24])[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:25]([O:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1)[C:26]#[C:27][CH3:28].C(N(CC)C(C)C)(C)C>ClCCl>[CH2:14]([N:11]1[CH2:12][CH2:13][C:8]([CH:2]([NH:1][S:36]([C:33]2[CH:32]=[CH:31][C:30]([O:29][CH2:25][C:26]#[C:27][CH3:28])=[CH:35][CH:34]=2)(=[O:38])=[O:37])[C:3]([O:5][CH2:6][CH3:7])=[O:4])([S:21][CH2:22][CH2:23][OH:24])[CH2:9][CH2:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 59756971HCID 59756971, compound

Product 1

HCID 59756970HCID 59756970, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl amino{1-benzyl-4-[(2-hydroxyethyl)sulfanyl]-4-piperidinyl}acetate (2.1 g, 5 mmol) and 4-but-2-ynyloxy benzenesulfonyl chloride (1.24 g, 5.1 mmol) in dichloromethane (200 ml) at 0° C., N,N-diisopropylethylamine (3.0 g, 23.6 mmol) was added slowly. After the addition, the reaction mixture was stirred at room temperature for 4 h and quenched with water. The reaction mixture was washed with water, dried over anhydrous MgSO4, filtered and concentrated. It was purified by silica gel column chromatography eluting with 80% ethyl acetate:hexane to give ethyl {1-benzyl-4-[(2-hydroxyethyl)sulfanyl]-4-piperidinyl}({[4-(2-butynyloxy)phenyl]sulfonyl}amino)acetate as a brown oil; Yield: 1.0 g (85%); Electrospray Mass Spec: 561 (M+H)+.

Workup

  1. additionAfter the addition
  2. customquenched with water
  3. washThe reaction mixture was washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customIt was purified by silica gel column chromatography
  8. washeluting with 80% ethyl acetate

Sources & evidence

ORD record
ord-f6bede97abe64f1798983d1b3e421b2c
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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