1-Hydroxybenzotriazole → HCID 57779768, compound

HRID 1364197Notes

Reaction equation

HRID 1364197 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH3:45][C:46]([O:49][C:50]([NH:52][C@@H:53]([C:65](O)=[O:66])[CH2:54][C:55]1[C:60]([C:61]([F:64])([F:63])[F:62])=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:51])([CH3:48])[CH3:47]>ClCCl.O>[C:46]([O:49][C:50](=[O:51])[NH:52][C@@H:53]([C:65](=[O:66])[NH:1][CH:2]1[C:3](=[O:13])[NH:4][C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[CH2:7][CH2:8]1)[CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][C:60]=1[C:61]([F:64])([F:63])[F:62])([CH3:45])([CH3:48])[CH3:47]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44344333-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-oneHCID 7010037(R)-2-((tert-butoxycarbonyl)amino)-3-(2-(trifluoromethyl)phenyl)propanoic acid

Product 1

HCID 57779768HCID 57779768, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of racemic 3-amino-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (0.100 g, 0.57 mmol) in dichloromethane (5.0 mL) were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.218 g, 1.13 mmol), 1-hydroxybenzotriazole (0.153 g, 1.13 mmol), diisopropylethylamine (0.20 mL, 1.13 mmol) and N-Boc-D-2-trifluoromethyl phenylalanine (0.189 g, 0.57 mmol). The resulting mixture was stirred at room temperature for 18 hours, then diluted with H2O and extracted with ethyl acetate. The organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via prepatory thin-layer chromatography on silica gel (50% ethyl acetate/hexanes) to give the desired product.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an oil that
  6. customwas purified via prepatory thin-layer chromatography on silica gel (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-54e20a685d4f4cf889ff2dfb8cca8dac
Source dataset
uspto-grants-2011_02
Patent number
US07888345B2

Reaction notes

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