Benzylamine → HCID 90962418, compound

HRID 1093925Notes

Reaction equation

HRID 1093925 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:22]([NH:29][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66637583HCID 66637583, compound

Product 1

HCID 90962418HCID 90962418, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude N-t-butoxycarbonyl-(S)-2-amino-5-(1-piperidinyl)pentanoic acid (22.2 mg, 0.074 mmol) in anhydrous methylene chloride (0.50 mL) were added benzyl amine (9.7 mg, 0.091 mmmol) and 1-hydroxybenzotriazol monohydrate (11.1 mg, 0.082 mmol). To the reaction mixture stirred under ice-cold condition was added 1,3-dicyclohexylcarbodiimide (18.0 mg, 0.087 mmol), and the mixture was stirred for 0.5 hour. After removal of the ice bath, the mixture was stirred for 16 hours at room temperature, and then chloroform (20 mL) was added. The organic phase was washed with saturated aqueous sodium hydrogencarbonate solution (2×3 mL), dried over anhydrous sodium sulfate, and concentrated under vacuum to obtain a crude oily material (47 . 7 mg). The crude oil was purified by column chromatography (silica gel 2g, about 15% ammonia/methanol-chloroform (1:100)) to obtain N-t-butoxycarbonyl-(S)-2-amino-5-(1-piperidinyl)pentanoic acid benzyl amide (26.2 mg) as a colorless oily material [yield 90% from N-t-butoxycarbonyl-(S)-2-amino-5-(1-piperidinyl)pentanoic acid benzyl ether].

Workup

  1. stirringthe mixture was stirred for 0.5 hour
  2. customAfter removal of the ice bath
  3. stirringthe mixture was stirred for 16 hours at room temperature
  4. additionchloroform (20 mL) was added
  5. washThe organic phase was washed with saturated aqueous sodium hydrogencarbonate solution (2×3 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customto obtain a crude oily material (47 . 7 mg)
  9. customThe crude oil was purified by column chromatography (silica gel 2g, about 15% ammonia/methanol-chloroform (1:100))

Sources & evidence

ORD record
ord-7a226c95905b4337919fdb38e428e703
Source dataset
uspto-grants-2012_03
Patent number
US08133864B2

Reaction notes

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