Hydrochloric Acid → HCID 118308925, compound

HRID 1481987Notes

Reaction equation

HRID 1481987 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([NH:15][NH:16]C(OC(C)(C)C)=O)=[O:14])[CH2:2][CH:3]=[CH2:4].[ClH:24]>O1CCOCC1>[ClH:24].[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([NH:15][NH2:16])=[O:14])[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118319911Hydrazinecarboxylic acid, 2-[2-[2-(3-buten-1-yloxy)phenyl]acetyl]-, 1,1-dimethylethyl ester

Product 1

HCID 118308925HCID 118308925, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-(2-(2-(but-3-en-1-yloxy)phenyl)acetyl)hydrazinecarboxylate (0.28 g, 0.874 mmol, 1 equiv) was treated with 4 N HCl in dioxane (9 mL). After stirring 18 h, the reaction was concentrated in vacuo. The crude product was triturated with ether to provide the product (0.16 g, 71%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 7.28 (td, J=7.9, 1.8 Hz, 1H), 7.22 (dd, J=7.5, 1.3 Hz, 1H), 6.98 (d, J=8.3 Hz, 1H), 6.93 (t, J=7.5 Hz, 1H), 5.95 (ddt, J=17.2, 10.3, 6.8 Hz, 1H), 5.18 (dd, J=17.2, 1.6 Hz, 1H), 5.11 (d, J=10.3 Hz, 1H), 4.06 (t, J=6.7 Hz, 2H), 3.63 (s, 2H), 2.56 (q, J=6.6 Hz, 2H); LCMS (ESI, M+1): 221.15.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customThe crude product was triturated with ether

Sources & evidence

ORD record
ord-8df84165bbec4457b74c4c8e5917c00e
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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