Hydrochloric Acid → 2-{[(1R)-3-amino-1-(2-thiazolyl)propyl]oxy}-4-chlorobenzonitrile hydrochloride

HRID 2179953Notes

Reaction equation

HRID 2179953 reaction equation
CC(OC(=O)[NH:7][CH2:8][CH2:9][C@@H:10]([O:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[C:24]#[N:25])[C:11]1[S:12][CH:13]=[CH:14][N:15]=1)(C)C.Cl>O1CCOCC1>[ClH:23].[NH2:7][CH2:8][CH2:9][C@@H:10]([O:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[C:24]#[N:25])[C:11]1[S:12][CH:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69804096[(3R)-3-(5-Chloro-2-cyanophenoxy)-3-(2-thiazolyl)propyl]carbamic acid 1,1-dimethylethyl ester

Product 1

HCID 698000332-{[(1R)-3-amino-1-(2-thiazolyl)propyl]oxy}-4-chlorobenzonitrile hydrochlorideYield 178.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of [(3R)-3-(5-chloro-2-cyanophenoxy)-3-(2-thiazolyl)propyl]-carbamic acid 1,1-dimethylethyl ester (140 mg, 0.36 mmol) in dry dioxan (3 ml) was added 4M HCl in dioxan (1 ml) and the mixture was stirred at room temperature for 16 h. The precipitate was collected, washed with ethyl acetate and vacuum dried to leave 106 mg of a white solid (90%).

Workup

  1. customThe precipitate was collected
  2. washwashed with ethyl acetate and vacuum
  3. customdried

Sources & evidence

ORD record
ord-6561f046e78446d6a23515120c2dc4c6
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

Loading…