HCID 22626999, compound → Ethyl-4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-1-(4-{[(3-chloroanilino)carbonyl]oxy}-2-butynyl)-4-piperidinecarboxylate

HRID 278343Notes

Reaction equation

HRID 278343 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].ClCC#CC[N:32]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=1)[C:33](=[O:35])[O-:34]>>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH2:7][CH2:8][N:9]([CH2:4][C:6]#[C:7][CH2:8][O:34][C:33]([NH:32][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)=[O:35])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 22626999HCID 22626999, compoundHCID 235139014-Chloro-2-butynyl-(3-chlorophenyl)carbamate

Product 1

HCID 23513859Ethyl-4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-1-(4-{[(3-chloroanilino)carbonyl]oxy}-2-butynyl)-4-piperidinecarboxylateYield 128.3%

Procedure

Ethyl-4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-1-(4-{[(3 chloroanilino)carbonyl]oxy}-2-butynyl)-4-piperidinecarboxylate was prepared according to the general method as outlined in Example 37 (step 1). Starting from 4-[[[4-(2-Butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid ethyl ester (0.291 g,0.7 mmol) and 4-chloro-2-butynyl-(3-chlorophenyl)carbamate (0.19 g, 0.735), 0.27 g (64%) of the desired product was isolated as pale yellow oil. Electrospray Mass Spec: 601.3 (M+H)+

Workup

  1. customEthyl-4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-1-(4-{[(3 chloroanilino)carbonyl]oxy}-2-butynyl)-4-piperidinecarboxylate was prepared

Sources & evidence

ORD record
ord-70332c6084174b45b930f5587a43be63
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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