Triethylamine → Methyl 1-([1,1'-Biphenyl]-2-carbonyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate

HRID 1420586Notes

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.[C:35]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:36]([C:41](Cl)=[O:42])=[CH:37][CH:38]=[CH:39][CH:40]=1>C(Cl)Cl.O>[C:35]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:36]([C:41]([N:1]2[C:2]3[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=3[CH2:4][N:5]([S:13]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)(=[O:14])=[O:15])[CH:6]([C:7]([O:9][CH3:10])=[O:8])[CH2:11]2)=[O:42])=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 1.5 g (3.8 mmol) of methyl 2-[(2-aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate and 2.65 ml of triethylamine in 12 ml of CH2Cl2 chilled at 0° C. was added a solution of [1,1'-biphenyl]-2-carbonyl chloride in 6 ml of CH2Cl2. The mixture was stirred at room temperature overnight and diluted with CH2Cl2 and H2O. The organic layer was separated and 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 C31H28N2O6S: Calc'd: C,66.9; H,5.1; N,5.0; Found: C,67.3; H,5.2; N,4.7.

Workup

customThe organic layer was separated
washwashed with 2 N citric acid, brine and dried-with Na2SO4
customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-f809706250ff44c4947d275a22c7c0a1
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071903

Reaction notes

Loading…