Triethylamine → HCID 57206721, compound

HRID 747737Notes

Reaction equation

HRID 747737 reaction equation
C(O[C:6]([NH:8][C@@H:9]([CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7])(C)(C)C.[C:31]([C:33]1[CH:41]=[CH:40][C:36](C(O)=O)=[CH:35][CH:34]=1)#[N:32].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>Cl.O1CCOCC1.C(Cl)Cl>[C:31]([C:33]1[CH:41]=[CH:40][C:36]([C:6]([NH:8][C@@H:9]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])=[O:7])=[CH:35][CH:34]=1)#[N:32]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 120874-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57262441HCID 57262441, compound

Product 1

HCID 57206721HCID 57206721, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

1.12 g (2.73 mmol) of benzyl (2S)-2-t-butoxycarbonylamino-4-(3-cyanophenoxy)butanoate was dissolved in 10 ml of 4 N solution of hydrogen chloride in dioxane, and they were stirred at room temperature for 2 hours. The solvent was evaporated, and the obtained oily residue was dissolved in 14 ml of dichloromethane. 390 mg (2.73 mmol) of 4-cyanobenzoic acid, 405 mg (3.00 mmol) of HOBt, 0.83 ml (6.00 mmol) of triethylamine and 575 mg (3.00 mmol) of WSC.HCl were successively added to the solution under cooling with ice, and they were stirred at room temperature overnight. After the treatment with methylene chloride as the extractant in an ordinary manner, the title compound was obtained.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe obtained oily residue was dissolved in 14 ml of dichloromethane
  3. temperatureunder cooling with ice, and they
  4. stirringwere stirred at room temperature overnight

Sources & evidence

ORD record
ord-33bcb828e11d460aa890ab9127becc10
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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