Hydrochloric Acid → HCID 86585414, compound

HRID 278367Notes

Reaction equation

HRID 278367 reaction equation
[ClH:1].[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]2([C:22]([NH:24][OH:25])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)[C:3]#[C:4][CH3:5].BrC[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1.[CH2:38](N(CC)CC)C.Cl>CO.C(OCC)C>[ClH:1].[CH2:2]([O:6][C:7]1[CH:8]=[CH:9][C:10]([S:13]([C:16]2([C:22]([NH:24][OH:25])=[O:23])[CH2:21][CH2:20][N:19]([CH2:38][C:30]3[CH:29]=[CH:28][CH:37]=[CH:36][C:31]=3[C:32]([O:34][CH3:35])=[O:33])[CH2:18][CH2:17]2)(=[O:14])=[O:15])=[CH:11][CH:12]=1)[C:3]#[C:4][CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 256687Methyl 4-(bromomethyl)benzoateHCID 10134896HCID 10134896, compound

Product 1

HCID 86585414HCID 86585414, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 3283Diethyl EtherSolvent2×

Procedure

To 4-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-4-piperidinecarboxamide hydrochloride (prepared from Example 76) (2.5 g, 6.43 mmol) and methyl 4-(bromomethyl)benzoate (1.62 g, 7.07 mmol) in methanol (100 mL) at 50° C. was added triethylamine (2.25 mL, 16.1 mmol). After 30 min additional methanol (50 mL) was added. After 18 h the reaction mixture was concentrated in vacuo and 1N aqueous hydrochloric acid (10 mL) and water was added. The resulting solid was isolated and to it was added methanol (20 mL) and 1N hydrochloric acid in diethylether (15 mL). To the resulting solution was added diethyl ether. Trituration of the precipitate gave methyl ({4-{[4-(2-butynyloxy)phenyl]sulfonyl}-4-[(hydroxyamino)carbonyl]-1-piperidinyl}methyl)benzoate hydrochloride as a white powder (2.4 g). 1H NMR (dmso d6, 300 MHz) δ1.85 (t, 3H, CH3, J=2.2 Hz), 2.1-3.5 (m, 8H, CH2), 3.87 (S, 3H, OCH3), 4.40 (bd s, 2H, NCH2Ar), 4.89 (q, 2H, OCH2, J=2.2 Hz), 7.1-8.1 (m, 8H, ArH), 9.3-11.2 (m, 3H, NH, NHOH). Electrospray MS m/z 501.5 (M+H)+

Workup

  1. concentrationAfter 18 h the reaction mixture was concentrated in vacuo and 1N aqueous hydrochloric acid (10 mL) and water
  2. additionwas added
  3. customThe resulting solid was isolated and to it

Sources & evidence

ORD record
ord-0d97c4030ffd45e997d49d2cb1ef7416
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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