Diisopropylethylamine → HCID 59756970, compound

HRID 2084939Notes

Reaction equation

HRID 2084939 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-570ffcc6d171428eb60b1bc5cb1c22db
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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