Diisopropylethylamine → HCID 86621913, compound

HRID 1984553Notes

Reaction equation

HRID 1984553 reaction equation
N[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:26](=[O:34])[NH:27][CH2:28][CH2:29][C:30]([F:33])([F:32])[F:31])([CH2:23][CH2:24][CH3:25])[C:20]([OH:22])=O.O.O[N:37]1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[OH:18][C:19]([CH2:23][CH2:24][CH3:25])([C:20]([NH2:37])=[O:22])[C:26]([N:27]([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)[CH2:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[O:34]

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 57434481HCID 57434481, compound

Product 1

HCID 86621913HCID 86621913, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 135 mg (0.60 mmol) (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one, and 154 mg (0.60 mmol) (S or R )-2-hydroxy-2-(3,3,3-trifluoro-propylcarbamoyl)-pentanoic acid, entity B, in 10 ml tetrahydrofuran were cooled to 0° C. and 93.8 mg (0.60 mmol) 1-hydroxy-benzotriazole hydrate, 210 μl (1.20 mmol) diisopropylethylamine and 117 mg (0.60 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 ethylacetate/heptane (gradient 10:90 to 100:0) yielded 221 mg (80%) (S or R)-2-hydroxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-propyl-N-(3,3,3-trifluoro-propyl)-malonamide, entity B: MS (m/e): 462.0 (M−H)−.

Workup

  1. customRemoval of the solvent
  2. distillationby distillation and chromatography on silicagel with ethylacetate/heptane (gradient 10:90 to 100:0)

Sources & evidence

ORD record
ord-935fff9728a048b7b151d7a3fd909f09
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

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