Diisopropylethylamine → HCID 57713976, compound

HRID 1984546Notes

Reaction equation

HRID 1984546 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2.[OH:18][C:19]([C:25](=[O:32])[NH:26][CH2:27][C:28]([F:31])([F:30])[F:29])([CH2:23][CH3:24])[C:20](O)=[O:21].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[CH2:23]([C:19]([OH:18])([C:25]([NH:26][CH2:27][C:28]([F:30])([F:29])[F:31])=[O:32])[C:20]([NH:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2)=[O:21])[CH3:24]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 25067537(7S)-7-Amino-5,7-dihydro-6H-dibenzo[b,d]azepin-6-oneHCID 87260088HCID 87260088, compound

Product 1

HCID 57713976HCID 57713976, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 250 mg (1.12 mmol) (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one and 256 mg (1.12 mmol) (RS)-2-hydroxy-2-(2,2,2-trifluoro-ethylcarbamoyl)-butyric acid in 24 ml tetrahydrofuran were cooled to 0° C. and 174 mg (0.94 mmol) 1-hydroxy-benzotriazole hydrate, 390 μl (2.23 mmol) diisopropylethylamine and 218 mg (1.12 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride were added. Stirring was continued overnight at room temperature. Removal of the solvent by distillation and chromatography on silicagel with ethylacetate/heptane 2/8 yielded 330 mg (68%) (R/S)-2-ethyl-2-hydroxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-N′-(2,2,2-trifluoro-ethyl)-malonamide as a colorless oil, MS (m/e): 436.1 (M+H)+.

Workup

  1. customRemoval of the solvent
  2. distillationby distillation and chromatography on silicagel with ethylacetate/heptane 2/8

Sources & evidence

ORD record
ord-0b2a237134b44d51a447a88f754ac693
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

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