Hydrochloric Acid → HCID 23513882, compound

HRID 353584Notes

Reaction equation

HRID 353584 reaction equation
Cl.[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]2([C:33]([NH:35][OH:36])=[O:34])[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=3C(OC)=O)[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)[C:3]#[C:4][CH3:5].[OH-:37].[NH4+:38].Cl.[Cl:40][CH2:41]Cl>CO.C(OCC)C>[ClH:40].[NH2:38][C:41]([C:30]1[CH:31]=[CH:32][C:23]([CH2:22][N:19]2[CH2:18][CH2:17][C:16]([S:13]([C:10]3[CH:9]=[CH:8][C:7]([O:6][CH2:2][C:3]#[C:4][CH3:5])=[CH:12][CH:11]=3)(=[O:14])=[O:15])([C:33]([NH:35][OH:36])=[O:34])[CH2:21][CH2:20]2)=[CH:24][CH:29]=1)=[O:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 86585414HCID 86585414, compound

Product 1

HCID 23513882HCID 23513882, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To methyl ({4-{[4-(2-butynyloxy)phenyl]sulfonyl}-4-[(hydroxyamino)carbonyl]-1-piperidinyl}methyl)benzoate hydrochloride (from example 77) (0.20 g) in methanol (10 mL) was added concentrated aqueous ammonium hydroxide (4 mL). After several weeks the reaction mixture was concentrated in vacuo and chromatographed on silica gel (methanol/dichloromethane) to give a white powder which was dissolved in dichloromethane and methanol. 1N Hydrochloric acid in diethylether was added followed by additional diethylether. Trituration gave 1-[4-(aminocarbonyl)benzyl]-4-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-4-piperidinecarboxamide hydrochloride as a white powder (0.106 g). 1H NMR (Dmso d6, 300 MHz) δ1.85 (t, 3H, CH3, J=2.2 Hz), 2.2-3.5 (m, 811, CH2), 4.33 (bd s, 2H, NCH2Ar), 4.89 (q, 2H, OCH2, J=2.2 Hz), 7.1-8.0 (m, 8H, ArH), 7.47 (s, 1H, CONH), 8.04 (s, 1H, CONH), 9.35 (bd s, 1H, NHOH), 10.44 (bd s, 1H, NHOH), 11.1 (s, 1H, NH). Electrospray MS m/z 486.3 (M+H)+.

Workup

  1. concentrationAfter several weeks the reaction mixture was concentrated in vacuo
  2. customchromatographed on silica gel (methanol/dichloromethane)
  3. customto give a white powder which

Sources & evidence

ORD record
ord-092a93bbf0564e9f8c24d8224a379673
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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