1,2-Dichloroethane → (S)-N-[(S)-5-(2-Benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2-hydroxy-propionamide

HRID 31001

Reaction equation

[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:10][CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]2[CH:20]=[CH:21][CH:22]=[CH:23][C:5]=2[C:4]2[CH:24]=[CH:25][CH:26]=[CH:27][C:3]1=2.[C:28](O)(=[O:32])[C@H:29]([CH3:31])[OH:30].ON1C2C=CC=CC=2N=N1.C(Cl)CCl>C1COCC1.O.C(OCC)(=O)C>[CH2:13]([O:12][CH2:11][CH2:10][N:7]1[C:8](=[O:9])[C@@H:2]([NH:1][C:28](=[O:32])[C@@H:29]([OH:30])[CH3:31])[C:3]2[CH:27]=[CH:26][CH:25]=[CH:24][C:4]=2[C:5]2[CH:23]=[CH:22][CH:21]=[CH:20][C:6]1=2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-7-Amino-5-(2-benzyloxy-ethyl)-5H,7H-dibenzo[b,d]azepin-6-one (50 mg, 0.14 mmol) and L-(+)-lactic acid (14 mg, 0.15 mmol) were dissolved in THF (2 ml), cooled to 0° C. and under exclusion of moisture subsequently treated with 1-hydroxybenzotriazole (21 mg, 0.15 mmol), EDC (33 mg, 0.17 mmol) and N-diisopropyl-ethylamine (0.05 ml, 0.28 mmol). After stirring for 30 min. at 0° C. and 3 h at ambient temperature, the mixture was diluted with water and ethyl acetate (10 ml each), the phases separated and the organic layer extracted with water, 1N aqueous HCl and saturated aqueous NaCl. After drying over magnesium sulphate and evaporation of the solvent, the title compound was afforded as colourless oil (98%). MS: m/e=431(M−H+).

Workup

customthe phases separated
extractionthe organic layer extracted with water, 1N aqueous HCl and saturated aqueous NaCl
dry with materialAfter drying over magnesium sulphate and evaporation of the solvent

Sources & evidence

ORD record: ord-8da343e23cc24acd828e859b0586d42e
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425551B2

Linked notes

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