Triethylamine hydrochloride → HCID 178500791, compound

HRID 1634709Notes

Reaction equation

HRID 1634709 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][CH2:8][N:9]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.[N-:29]=[N+:30]=[N-:31].[Na+].Cl.C(N(CC)CC)C>COCCOC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N:9]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[NH:31][N:30]=[N:29][N:26]=3)=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 18678876HCID 18678876, compound

Product 1

HCID 178500791HCID 178500791, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of methyl 3-[(4-methoxyphenethyl)-(4-cyanobenzenesulfonyl)-amino]-propionate (220 mg, 0.55 mmol), sodium azide (43 mg, 0.66 mmol), and triethylamine hydrochloride (91 mg, 0.66 mmol) in anhydrous ethylene glycol dimethyl ether (3 mL) was fluxed for 48 h. Reaction mixture was concentrated, resuspended in water (10 mL) and extracted with ethyl acetate (2×20 mL). The organic layer was washed with 0.5 N HCl solution and brine, dried over MgSO4. After filtration, the filtrate was concentrated to give methyl 3-[(4-methoxyphenethyl)-(4-(tetrazol-5yl)benzenesulfonyl)-amino]-propionate (112 mg, 0.25 mmol).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washThe organic layer was washed with 0.5 N HCl solution and brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-01a3775952164843a2377aaaf402ab22
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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