Hydrochloric Acid → (S)-2-amino-N-(2-(benzo[d]oxazol-2-ylamino)ethyl)pent-4-ynamide hydrochloride

HRID 447147Notes

Reaction equation

HRID 447147 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:27])[C@@H:15]([NH:19]C(=O)OC(C)(C)C)[CH2:16][C:17]#[CH:18].[ClH:28]>O1CCOCC1>[ClH:28].[NH2:19][C@@H:15]([CH2:16][C:17]#[CH:18])[C:14]([NH:13][CH2:12][CH2:11][NH:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)=[O:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86654767(S)-tert-Butyl 1-(2-(benzo[d]oxazol-2-ylamino)ethylamino)-1-oxopent-4-yn-2-ylcarbamate

Product 1

HCID 86654766(S)-2-amino-N-(2-(benzo[d]oxazol-2-ylamino)ethyl)pent-4-ynamide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

(S)-tert-Butyl 1-(2-(benzo[d]oxazol-2-ylamino)ethylamino)-1-oxopent-4-yn-2-ylcarbamate (99.5 mg, 0.267 mmol) was dissolved in 1,4-dioxane (3.5 mL) and treated with 4N HCl in 1,4-dioxane (3.5 mL). The resulting mixture was stirred for 2.5 h and a solid separated from the solution. HCl in 1,4-dioxane (1 mL) was added and the resulting mixture was stirred for 3 h. The solid product was collected by filtration, washed with 1,4-dioxane, then dried in vacuum oven for 1 day at room temperature to yield the title compound as its corresponding hydrochloride salt, as a white solid.

Workup

  1. customa solid separated from the solution
  2. additionHCl in 1,4-dioxane (1 mL) was added
  3. stirringthe resulting mixture was stirred for 3 h
  4. filtrationThe solid product was collected by filtration
  5. washwashed with 1,4-dioxane
  6. customdried in vacuum oven for 1 day at room temperature

Sources & evidence

ORD record
ord-523bb5ea0b984600b7ca075a3ffe822f
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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