Diisopropylethylamine → HCID 57713983, compound

HRID 1984556Notes

Reaction equation

HRID 1984556 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.[CH3:18][O:19][C:20](=[O:30])[C:21]([OH:29])([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22](O)=[O:23].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[CH3:18][O:19][C:20](=[O:30])[C:21]([OH:29])([C:22](=[O:23])[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)[CH2:25][CH:26]([CH3:28])[CH3:27]

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 57713984HCID 57713984, compound

Product 1

HCID 57713983HCID 57713983, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 350 mg (1.56 mmol) (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one and 327 mg (1.72 mmol) (R/S)-2-hydroxy-2-isobutyl-malonic acid monomethyl ester in 30 ml tetrahydrofuran were cooled to 0° C. and 232 mg (1.72 mmol) 1-hydroxy-benzotriazole hydrate, 584 μl (3.43 mmol) diisopropylethylamine and 329 mg (192 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride were added. Stirring was continued overnight at room temperature. Extraction with water/ethylacetate and chromatography on silicagel with heptane/ethylacetate (gradient 90/10 to 50/50) yielded 470 mg (76%) (R/S)-2-hydroxy-4-methyl-2-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-pentanoic acid methyl ester as a colorless foam, MS (m/e): 397.3 (M+H)+.

Workup

  1. extractionExtraction with water/ethylacetate and chromatography on silicagel with heptane/ethylacetate (gradient 90/10 to 50/50)

Sources & evidence

ORD record
ord-aee52e4f1d3e44808172276beb5920d2
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

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