Triethylamine → HCID 66791478, compound

HRID 1096591Notes

Reaction equation

HRID 1096591 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=2)[CH2:3]1.[C:17]([O:21][C:22]([NH:24][C@H:25]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[CH2:26][C:27](O)=[O:28])=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[NH:12]1[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=[C:8]1[CH:4]1[CH2:5][CH2:6][CH2:7][N:2]([C:27](=[O:28])[CH2:26][C@H:25]([NH:24][C:22](=[O:23])[O:21][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:30][C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[CH2:3]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7021567(βR)-4-Chloro-β-[[(1,1-dimethylethoxy)carbonyl]amino]benzenebutanoic acidHCID 534298372-(Piperidin-3-yl)-1H-benzimidazole--hydrogen chloride (1/1)

Product 1

HCID 66791478HCID 66791478, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a flask containing 2-(piperidin-3-yl)-1H-benzo[d]imidazole hydrochloride (200.0 mg, 0.841 mmol) and (R)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl) butanoic acid (282.5 mg, 0.900 mmol) was added dichloromethane (5 mL) and triethylamine (0.23 mL, 1.683 mmol); the reaction mixture was stirred at room temperature until all the components dissolved. To the solution was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (193.5 mg, 1.010 mmol) followed by N-hydroxybenzotriazole (142.1 mg, 1.052 mmol). The solution was stirred at ambient temperature for 12 hrs and diluted with excess DCM (5 mL). The solution was washed with water (2×8 mL) and brine (lx 5 mL), and then the organic layer was collected, dried with Na2SO4, and concentrated to yield tert-butyl (2R)-4-(3-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-1-(4-chlorophenyl)-4-oxobutan-2-ylcarbamate (3A) as an amorphous solid (415.9 mg, 99.5% yield). ESI-MS: m/z 497.4 (M+H)+.

Workup

  1. dissolutiondissolved
  2. stirringThe solution was stirred at ambient temperature for 12 hrs
  3. washThe solution was washed with water (2×8 mL) and brine (lx 5 mL)
  4. customthe organic layer was collected
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c3f8d99a29a4cfa997bf4ea9cb3a65c
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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