Hydrochloric Acid → HCID 67076832, compound

HRID 1675678Notes

Reaction equation

HRID 1675678 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:28])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][C:15]1[CH:27]=[CH:26][C:18]([C:19]([O:21]C(C)(C)C)=[O:20])=[CH:17][CH:16]=1)=[O:13].[ClH:29].O1CCOCC1>ClCCl>[ClH:29].[OH:1][CH2:2][CH2:3][N:4]([CH3:28])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][C:15]1[CH:27]=[CH:26][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58024758HCID 58024758, compound2×

Product 1

HCID 67076832HCID 67076832, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-({8-[(2-hydroxyethyl)(methyl)amino]octanoyl}amino)-benzoate (28.4 g, 72.4 mmol, e.g. which can be as prepared in Intermediate 38) in dry dichloromethane (225 ml) was added a 4M hydrogen chloride solution in 1,4-dioxane (145 ml, 579 mmol, 8 equivalents). The mixture quickly became cloudy and was stirred overnight resulting in a uniform white suspension. The solvents were evaporated off in vacuo, using a high vacuum at the end, to give the title compound (23.45 g) as a white solid. LCMS showed positive ion at m/z 336; TRET=2.01 min. NMR (d6-DMSO) appeared to show a trace of dichloromethane and 1,4-dioxane in the product.

Workup

  1. customresulting in a uniform white suspension
  2. customThe solvents were evaporated off in vacuo

Sources & evidence

ORD record
ord-e671f0fbe57141dea03f0af5a522a709
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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