Benzylamine → HCID 89668657, compound

HRID 1482373Notes

Reaction equation

HRID 1482373 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([OH:16])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:46]([NH2:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C=O)C.[Cl-].[Na+].O.CCCCCC.C(OCC)(=O)C>[CH2:46]([NH:53][C:14](=[O:16])[C@@H:2]([NH:1][C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[C:10]([F:11])([F:12])[F:13])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

9

Reactant 4

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7009540N~2~-(tert-Butoxycarbonyl)-N~6~-(trifluoroacetyl)-L-lysine

Product 1

HCID 89668657HCID 89668657, compoundYield 102.5%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of Boc-Lys(Tfa)-OH (Compound tk96) (104 mg, 0.304 mmol) and 1H-benzo[d][1,2,3]triazol-1-ol (HOBT) (61.6 mg, 0.456 mmol) in DMF (0.5 mL) was cooled in an ice bath under a nitrogen atmosphere, followed by addition of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSCI.HCl) (87 mg, 0.456 mmol). The reaction mixture was stirred at the same temperature for 5 minutes, followed by addition of benzylamine (40 μL, 0.365 mmol). The reaction mixture was stirred at room temperature for 17.5 hours, followed by addition of ethyl acetate, hexane and brine. The resulting mixture was extracted with ethyl acetate, and the organic phase was washed with brine (1 mL×2) and then dried over sodium sulfate. Following concentration under reduced pressure, the resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate) to afford (S)-tert-butyl (1-(benzylamino)-1-oxo-6-(2,2,2-trifluoroacetamido)hexan-2-yl)carbamate (Compound tk97) (134.4 mg, quant.).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 17.5 hours
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with brine (1 mL×2)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d754ab6eaa5f41bcad0dec5eab050dce
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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