Hydrochloric Acid → (2R)-2-[4-(2-Aminoethoxy)phenyl]-2-({[4-(2-butynyloxy)phenyl]sulfonyl)amino)-N-hydroxyethanamide

HRID 1976442Notes

Reaction equation

HRID 1976442 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C@H:16]([C:21]2[CH:37]=[CH:36][C:24]([O:25][CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)=[CH:23][CH:22]=2)[C:17]([NH:19][OH:20])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].Cl>ClCCl.CCOCC>[NH2:28][CH2:27][CH2:26][O:25][C:24]1[CH:36]=[CH:37][C:21]([C@@H:16]([NH:15][S:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:11][CH:10]=2)(=[O:14])=[O:13])[C:17]([NH:19][OH:20])=[O:18])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54233279tert-butyl 2-{4-[(1R)-1-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-2-(hydroxyamino)-2-oxoethyl]phenoxy}ethylcarbamate2×

Product 1

HCID 10320652(2R)-2-[4-(2-Aminoethoxy)phenyl]-2-({[4-(2-butynyloxy)phenyl]sulfonyl)amino)-N-hydroxyethanamideYield 98.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Through a solution of 0.354 g (0.664 mmol) of the product of Example 199, tert-butyl 2-{4-[(1R)-1-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-2-(hydroxyamino)-2-oxoethyl]phenoxy}ethylcarbamate, in 10 mL of dichloromethane was bubbled hydrogen chloride gas for 10 minutes. The reaction was stoppered and let sit at room temperature for 30 minutes. The reaction was then diluted with 15 mL of ether and the resulting white precipitate was collected by filtration and dried in vacuo to give 0.283 g of (2R)-2-[4-(2-Aminoethoxy)phenyl]-2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-N-hydroxyethanamide as a white solid. Electrospray Mass Spec 434.3 (M+H)+

Workup

  1. filtrationthe resulting white precipitate was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-d1de154a74d644a589e2de2543757a57
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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