Hydrochloric Acid → tert-Butyl propiolate

HRID 14282

Reaction equation

HRID 14282 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.CO.O1CCO[CH2:39][CH2:38]1>>[C:6]([C:38]#[CH:39])([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:33]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 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 106%

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-3966842eb8514e45bf5f87df9672af39
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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