Triethylamine → Methyl 4-(4-Methoxybenzenesulfonyl)-1-(2-methyl-5-fluorobenzoyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate

HRID 1420587Notes

Reaction equation

[NH2:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:6]([CH2:11]O)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[CH3:35][C:36]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:37]=1[C:38](Cl)=[O:39]>C(Cl)Cl.O>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([N:5]2[CH2:4][C:3]3[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=3[N:1]([C:38](=[O:39])[C:37]3[CH:41]=[C:42]([F:45])[CH:43]=[CH:44][C:36]=3[CH3:35])[CH2:11][CH:6]2[C:7]([O:9][CH3:10])=[O:8])(=[O:15])=[O:14])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 1.5 g (3.80 mmol) of methyl 2-[(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate and 2.64 ml (18.97 mmol) of triethylamine in 15 ml of CH2Cl2, chilled to 0° C., was added 1.36 g (11.4 mmol) of 2-methyl-5-fluorobenzoyl chloride. The mixture was stirred at room temperature overnight. The solution was then diluted with CH2Cl2 and water and the organic layer separated. The organic layer was washed with 2 N citric acid, brine and dried with Na2SO4. The solvent was removed under vacuum to give 2.2 g of a white foam. Anal. for C26H25FN2O6S: Calc'd: C,60.9; H,4.9; N,5.5; Found: C,60.9; H,5.0; N,5.0; Mass spectrum (ES) 513.4 (M+H).

Workup

customthe organic layer separated
washThe organic layer was washed with 2 N citric acid, brine
dry with materialdried with Na2SO4
customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-ac129c08bd1947869be5fa7988e36c4a
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071903

Reaction notes

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