1-Hydroxybenzotriazole → HCID 58739163, compound

HRID 720274Notes

Reaction equation

HRID 720274 reaction equation
C(OC([NH:8][C@@H:9]([CH3:13])[C:10](O)=[O:11])=O)(C)(C)C.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]([C@@H:26]([NH2:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)[CH:15]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH2:8][C@@H:9]([CH3:13])[C:10]([NH:28][C@H:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)[CH:21]=1)[CH3:27])=[O:11]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57419702HCID 57419702, compound

Product 1

HCID 58739163HCID 58739163, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-2-tert-butoxycarbonylamino-propionic acid (0.083 mmol), (S)-1-(3-pyridin-3-yl-phenyl)-ethylamine (12.7 mg, 0.064 mmol), EDAC.HCl (18.4 mg, 0.096 mmol), HOBT (13 mg, 0.096 mmol and d iisopropylethylamine (33 μL, 0.192 mmol) ) in DMF (2 mL) was stirred at room temperature for 18 h. The reaction mixture was purified by preparative HPLC (Primeshere C18-HC 21.2×100 mm; (5 mM NH4OAc ) 0–100% gradient over 5 min; 20 mL/min flow rate). The solvents were removed through evaporation on the speed-vac, and the crude product was dissolved in CH2Cl2/TFA (1: 1, 2 mL) and stirred at room temperature for 3 h. The reaction mixture was concentrated on the speed-vac and purified by preparative HPLC (5 mM NH4OAc buffer; gradient 0% to 100% B in 10 min (A: 10% CH3CN/H2O; B: 90% CH3CN/H2O; column: Primesphere C18 HC 21.2×100 mm) to afford the title product.

Workup

  1. customThe reaction mixture was purified by preparative HPLC (Primeshere C18-HC 21.2×100 mm
  2. wait(5 mM NH4OAc ) 0–100% gradient over 5 min
  3. customThe solvents were removed through evaporation on the speed-vac
  4. dissolutionthe crude product was dissolved in CH2Cl2/TFA (1: 1, 2 mL)
  5. stirringstirred at room temperature for 3 h
  6. concentrationThe reaction mixture was concentrated on the speed-vac
  7. custompurified by preparative HPLC (5 mM NH4OAc buffer
  8. waitgradient 0% to 100% B in 10 min (A: 10% CH3CN/H2O

Sources & evidence

ORD record
ord-aba833b5d6044b3eac17f12ee7fc1f7c
Source dataset
uspto-grants-2006_11
Patent number
US07135472B2

Reaction notes

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