Diisopropylethylamine → (S)-2-hydroxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-propionamide

HRID 1374568Notes

Reaction equation

HRID 1374568 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.[C:18](O)(=[O:22])[C@H:19]([CH3:21])[OH:20].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[OH:20][C@@H:19]([CH3:21])[C:18]([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:22]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 107689L-Lactic AcidHCID 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-one

Product 1

HCID 69507451(S)-2-hydroxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-propionamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.20 g (0.9 mmol) (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one in 8 ml tetrahydrofurane was treated at 0° C. with 0.09 g (0.99 mmol) L-lactic acid, 0.14 g (0.9 mmol) 1-hydroxybenzotriazole hydrate, 314 μl (1.8 mmol) N-ethyldiisopropylamine and 0.18 g (0.9 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochlorid. After stirring at room temperature overnight the mixture was extracted with 1N aqueous hydrochloric acid/ethylacetate. Purification by chromatography on silicagel with ethylacetate/cyclohexane (0-100/100-0) yielded 0.19 g (70%) (S)-2-hydroxy-N—((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-propionamide as white solid; MS: m/e: 297.1 (M+H+).

Workup

  1. extractionwas extracted with 1N aqueous hydrochloric acid/ethylacetate
  2. customPurification by chromatography on silicagel with ethylacetate/cyclohexane (0-100/100-0)

Sources & evidence

ORD record
ord-75cf4134a827485e84c09d26f7c0a949
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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