Hydrochloric Acid → HCID 13818605, compound

HRID 2096106Notes

Reaction equation

HRID 2096106 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C)CCCN=C=NCC.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH2:52][C@H:53]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:54][CH:55]([CH3:57])[CH3:56]>C(Cl)Cl.CCOC(C)=O>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:52][C@H:53]([C:58]([O:60][C:61]([CH3:63])([CH3:62])[CH3:64])=[O:59])[CH2:54][CH:55]([CH3:57])[CH3:56])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 181649HOAtHCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoate

Product 1

HCID 13818605HCID 13818605, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

500 mg (1.7 mmol) Z-Phe-OH was dissolved in 10 mL of CH2Cl2. Subsequently, 415 mg N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide.HCl (EDCl, 2.2 mmol, 1.3 eq), 250 mg 7-aza-N-hydroxybenzatriazole (HOAt, 1.8 mmol, 1.1 eq), 478 μL triethylamine (TEA, 1.8 mmol, 1.1 eq) and 344 mg H-Leu-OtBu (1.8 mmol, 1.1 eq) were added. The reaction mixture was stirred at ambient temperature for 20 h. Subsequently, 20 mL EtOAc was added and the organic mixture was washed with 15 mL saturated aqueous Na2CO3 (2×), 15 mL saturated aqueous NaHCO3 (2×), 15 mL brine, dried (Na2SO4), concentrated in vacuo and co-evaporated with 10 mL toluene

Workup

  1. washthe organic mixture was washed with 15 mL saturated aqueous Na2CO3 (2×), 15 mL saturated aqueous NaHCO3 (2×), 15 mL brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo and co-evaporated with 10 mL toluene

Sources & evidence

ORD record
ord-1e0e7fee589f4b618695d01509d08a3a
Source dataset
uspto-grants-2013_05
Patent number
US08450084B2

Reaction notes

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