Hydrochloric Acid → HCID 118436420, compound

HRID 1775487Notes

Reaction equation

HRID 1775487 reaction equation
[ClH:1].O1CCOCC1.[CH3:8][O:9][C:10]1[CH:30]=[CH:29][C:13]([C:14]([O:16][CH2:17][C:18]([NH:21]C(OC(C)(C)C)=O)([CH3:20])[CH3:19])=[O:15])=[CH:12][CH:11]=1>C(Cl)Cl>[ClH:1].[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH2:17][C:18]([NH2:21])([CH3:20])[CH3:19])=[O:15])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118436175HCID 118436175, compound

Product 1

HCID 118436420HCID 118436420, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of hydrochloric acid in dioxane (5.0 mL, 20.0 mmol) was added to a solution of 2-[(tert-butoxycarbonyl)amino]-2-methylpropyl 4-methoxybenzoate (0.32 g, 1.0 mmol) in DCM (10 mL) and the mixture was stirred for 1.5 h at room temperature. The reaction mixture was concentrated to give the title compound (0.26 g, 100%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.32 (br s, 3 H), 8.11 (m, J=8.9 Hz, 2 H), 7.06 (m, J=8.9 Hz, 2 H), 4.24 (s, 2 H), 3.85 (s, 3 H), 1.35 (s, 6 H). m/z (APCI+) for C12H17NO3 224.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-bcc18ff74bbc4779869371d891fce104
Source dataset
uspto-grants-2016_02
Patent number
US09260439B2

Reaction notes

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