Hydrochloric Acid → tert-Butyl propiolate

HRID 349072

Reaction equation

HRID 349072 reaction equation
[C:1]([O:5][C:6](=[O:33])NC(CC1C=C(F)C=C(F)C=1)C(O)CNC1(C2C=CC=C(C#C)C=2)CC1)([CH3:4])([CH3:3])[CH3:2].Cl.O1CCO[CH2:37][CH2:36]1>CO>[C:6]([C:36]#[CH:37])([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 21062898[1-(3,5-Difluorobenzyl)-3-[1-(3-ethynylphenyl)cyclopropylamino]-2-hydroxypropyl]-carbamic acid tert-butyl ester

Product 1

HCID 543038tert-Butyl propiolateYield 360%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[1-(3,5-difluorobenzyl)-3-[1-(3-ethynylphenyl)cyclopropylamino]-2-hydroxypropyl]-carbamic acid tert-butyl ester (2.34 g, 5.13 mmol) was treated with 4N HCl in dioxane (15.8 mL, 63.3 mmol). The resulting heterogeneous mixture was treated with methanol (10 mL) whereupon it became homogeneous over 30 min. The volatiles were evaporated in vacuo. Dioxane (20 mL) was added and the mixture was evaporated in vacuo to produce a white solid (2.33 g, 106%).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. additionDioxane (20 mL) was added
  3. customthe mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-cd9b0323cdc74c188f142cd7af870c28
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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