Hydrochloric Acid → HCID 23513882, compound

HRID 278368Notes

Reaction equation

HRID 278368 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, 8H, 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, 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-c890f2e4d8b045a2809484c6df39f94a
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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