Pyridine → methyl (2R)-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl)({[4-(2-butynyloxy)phenyl]sulfonyl}amino)ethanoate

HRID 1976441Notes

Reaction equation

HRID 1976441 reaction equation
[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].N1C=CC=CC=1.[CH2:30]([O:34][C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1)[C:31]#[C:32][CH3:33]>C(Cl)(Cl)Cl.CCOCC>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C@@H:2]([NH:1][S:41]([C:38]2[CH:37]=[CH:36][C:35]([O:34][CH2:30][C:31]#[C:32][CH3:33])=[CH:40][CH:39]=2)(=[O:43])=[O:42])[C:3]([O:5][CH3:6])=[O:4])=[CH:12][CH:11]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 1049PyridineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 86587123methyl (2R)-amino(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl)ethanoate

Product 1

HCID 86590204methyl (2R)-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl)({[4-(2-butynyloxy)phenyl]sulfonyl}amino)ethanoateYield 61.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 0.682 g (2.10 mmol) of methyl (2R)-amino(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl)ethanoate dissolved in 10 mL of chloroform and 2.2 mL of pyridine was added 0.566 g (2.315 mmol) of 4-but-2-ynyloxy-benzenesulfonyl chloride. The reaction was stirred at room temperature for 15 h and then diluted with ether. The organics were washed with water, 5% HCl solution and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to provide 0.691 g of methyl (2R)-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl)({[4-(2-butynyloxy)phenyl]sulfonyl}amino)ethanoate as a white foam Electrospray Mass Spec 533.1 (M+H)+

Workup

  1. washThe organics were washed with water, 5% HCl solution and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-debef7abdc5f4f62a0a4e6fcc9f112de
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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