Hydrochloric Acid → HCID 86718988, compound

HRID 1746267Notes

Reaction equation

HRID 1746267 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17]C(=O)OC(C)(C)C)=[CH:13][CH:12]=1)[C:2]#[CH:3].Cl.O1CCOCC1>C(Cl)Cl>[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86718986HCID 86718986, compound

Product 1

HCID 86718988HCID 86718988, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)phenylcarbamate (I-7a: 1.91 g, 5.69 mmol) in CH2Cl2 (14.24 mL) was added 4N HCl in dioxane (14.24 mL, 56.9 mmol). The mixture was stirred at room temperature for 2 hours, concentrated in vacuo, followed by the addition of aqueous saturated sodium bicarbonate. The mixture was then extracted twice with ethyl acetate, dried over MgSO4, filtered, and concentrated in vacuo. 4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)aniline (I-7b) was used as is for next step. LC-MS (M+1) 236.1, t=0.87 minute.

Workup

  1. concentrationconcentrated in vacuo
  2. additionfollowed by the addition of aqueous saturated sodium bicarbonate
  3. extractionThe mixture was then extracted twice with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customLC-MS (M+1) 236.1, t=0.87 minute

Sources & evidence

ORD record
ord-c01eaaa7b1b14ab0862bf3da2f7fb342
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

Loading…