1-Hydroxybenzotriazole → HCID 178500824, compound

HRID 1633904Notes

Reaction equation

HRID 1633904 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:30]1C2C=CC=CC=2N=N1.Cl.CN(CCCN=C=NCC)C.[CH3:51][O:52][C:53](=[O:57])[CH2:54][CH2:55]N.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:30][CH:54]([CH3:55])[C:53]([O:52][CH3:51])=[O:57])=[O:25])=[CH:22][CH:21]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 192794Methyl beta-alanateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178453065HCID 178453065, compound

Product 1

HCID 178500824HCID 178500824, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Trans-4-{[N-(tert-butoxycarbonyl)-N-(4-tert-butylcyclohexyl)amino]methyl}benzoic acid (22.0 g, 56.5 mmol) and 1-hydroxybenzotriazole (8.6 g, 57.0 mmol, containing 12% w/w water) was dissolved in DMF (300 mL). N-Dimethylaminopropyl-N′-ethylcarbodiimide hydrochloride (10.9 g, 56.8 mmol), β-alanine methyl ester (8.4 g, 60 mmol) and diisopropylethylamine (25 mL, 142 mmol) were added and the clear solution stirred at 20° C. for 16 hours. Solvent was removed by rotary evaporation and the residual oil re-dissolved in ethyl acetate (500 mL). The organic phase was washed with 5% aqueous sodium hydrogen carbonate solution (2×500 mL), 0.5 M citric acid (2×250 mL) and brine before being dried with anhydrous Na2SO4. Solvent was removed and the residual oil evaporated twice from acetonitrile. The oil was used without further purification. Yield: 24.0 g (89%).

Workup

  1. customSolvent was removed by rotary evaporation
  2. dissolutionthe residual oil re-dissolved in ethyl acetate (500 mL)
  3. washThe organic phase was washed with 5% aqueous sodium hydrogen carbonate solution (2×500 mL), 0.5 M citric acid (2×250 mL) and brine
  4. dry with materialbefore being dried with anhydrous Na2SO4
  5. customSolvent was removed
  6. customthe residual oil evaporated twice from acetonitrile
  7. customThe oil was used without further purification

Sources & evidence

ORD record
ord-3718ba8a9fe8499db39d3fbf63640c14
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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