Triethylamine hydrochloride → HCID 178472549, compound

HRID 551211Notes

Reaction equation

HRID 551211 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:18][CH2:19][C:20]#[N:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:18][CH2:19][C:20]1[NH:24][N:23]=[N:22][N:21]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 67048530HCID 67048530, compound

Product 1

HCID 178472549HCID 178472549, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

3.20 g (11.0 mmol) ethyl (2S)-2-(benzyloxycarbonyl-amino)-4-cyano-butyrate are dissolved in 40 ml of toluene and 1.08 g (16.5 mmol) sodium azide and 2.28 g (16.5 mmol) triethylamine-hydrochloride are added. The reaction mixture is heated to 85° C. for 24 hours, cooled to ambient temperature and extracted with water. The combined aqueous phases are acidified to pH 2 with semiconc. hydrochloric acid, the resulting precipitate is suction filtered, washed with water and dried at 50° C.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with water
  3. filtrationfiltered
  4. washwashed with water
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-7a17325e064a49348b8aefe9f162e0a2
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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