Acetic Acid → HCID 118659372, compound

HRID 1477251Notes

Reaction equation

HRID 1477251 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]#[C:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:19](OC)=[O:20])=[CH:12][CH:11]=1.[NH2:28][OH:29].CC(O)=O>C(O)(C)C>[OH:29][NH:28][C:19](=[O:20])[C:18]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]#[C:8][C:7]#[C:6][C@@H:4]2[CH2:5][C@H:3]2[CH2:2][OH:1])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 787HydroxylamineHCID 118659548HCID 118659548, compound

Product 1

HCID 118659372HCID 118659372, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirring solution of methyl 4-(4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)phenyl)-2-methyl-2-(methylsulfonyl)butanoate (9.7) in isopropanol (1.3 mL) at 0° C. was added hydroxylamine (946 μL, 15.44 mmol, 50% in water) and the reaction was stirred at room temperature overnight. The reaction mixture was neutralized with AcOH (884 μL, 15.44 mmol) and concentrated under reduced pressure to give a crude, which was purified by RP-HPLC (0-30% ACN in water) to yield N-hydroxy-4-(4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (9, 22.6 mg, 22.6% yield). MS: m/z calcd for C20H23NO5S 389.13. found [M+H]+ 390.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a crude, which
  3. customwas purified by RP-HPLC (0-30% ACN in water)

Sources & evidence

ORD record
ord-8af51702782645f591238300199ec467
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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