Hydrochloric Acid → HCID 21304705, compound

HRID 2084953Notes

Reaction equation

HRID 2084953 reaction equation
Cl.[OH:2][NH:3][C:4]([C@H:6]1[C:11]([CH3:13])([CH3:12])[S:10][CH2:9][CH2:8][N:7]1[S:14]([C:17]1[CH:37]=[CH:36][C:20]([O:21][CH2:22][C:23]#[C:24][CH2:25][CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:5]>ClCCl.CO>[NH2:28][CH2:27][CH2:26][CH2:25][C:24]#[C:23][CH2:22][O:21][C:20]1[CH:36]=[CH:37][C:17]([S:14]([N:7]2[CH2:8][CH2:9][S:10][C:11]([CH3:12])([CH3:13])[C@@H:6]2[C:4]([NH:3][OH:2])=[O:5])(=[O:15])=[O:16])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 44409163HCID 44409163, compound

Product 1

HCID 21304705HCID 21304705, compoundYield 108.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride gas was bubbled into a solution of 0.104 g (0.192 mmol) of tert-butyl 6-[4-({(3S)-3-[(hydroxyamino)carbonyl]-2,2-dimethylthiomorpholinyl}sulfonyl)-phenoxy]-4-hexynylcarbamate in 6 mL of dichloromethane and 2 mL of methanol for 5 min, and the reaction was stoppered and let stand for 1 h and then concentrated in vacuo. The residue was triturated with ether to provide 0.092 g (100%) of (3S)-4-({4-[(6-amino-2-hexynyl)oxy]phenyl}sulfonyl)-N-hydroxy-2,2-dimethyl-3-thiomorpholine carboxamide as a cream solid. Electrospray Mass Spec: 442.1 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-b6ac9c3c38c444c59a46699b15632686
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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