Diisopropylethylamine → HCID 131727473, compound

HRID 1984563Notes

Reaction equation

HRID 1984563 reaction equation
[OH:1][C:2]([C:9](=[O:27])[NH:10][C@@H:11]1[C:17](=[O:18])[NH:16][C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]1=2)([CH2:6][CH2:7][CH3:8])[C:3](O)=[O:4].[F:28][C:29]([F:33])([CH3:32])[CH2:30]N.O.O[N:36]1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[F:28][C:29]([F:33])([CH3:32])[CH2:30][N:10]([C@@H:11]1[C:17](=[O:18])[NH:16][C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]1=2)[C:9](=[O:27])[C:2]([OH:1])([CH2:6][CH2:7][CH3:8])[C:3]([NH2:36])=[O:4]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2758356421-00-1HCID 27960291-Hydroxybenzotriazole hydrateHCID 57713962HCID 57713962, compound

Product 1

HCID 131727473HCID 131727473, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 50.0 mg (0.14 mmol) 2-hydroxy-2-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-pentanoic acid and 14.2 mg (0.15 mmol) 2,2-difluoropropylamine in 2.5 ml tetrahydrofuran were cooled to 0° C. and 20.2 mg (0.15 mmol) 1-hydroxy-benzotriazole hydrate, 39 μl (0.3 mmol) diisopropylethylamine and 28.6 mg (0.15 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride were added. Stirring was continued overnight. Removal of the solvent by distillation and chromatography on silicagel with heptane/ethylacetate (gradient 90:10 to 50:50) yielded 30.0 mg (50%) (R/S)-N-(2,2-Difluoro-propyl)-2-hydroxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-propyl-malonamide: MS (m/e): 446.1 (M+H)+.

Workup

  1. customRemoval of the solvent
  2. distillationby distillation and chromatography on silicagel with heptane/ethylacetate (gradient 90:10 to 50:50)

Sources & evidence

ORD record
ord-94a682e1d39c4e6fbcb9d03b6548f252
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

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