2,4,6-Triisopropylbenzenesulfonyl azide → 3-azido-1-(2,2,2-trifluoroethyl)-4-(2,4,6-trimethoxybenzyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5dione

HRID 2213340Notes

Reaction equation

[F:1][C:2]([F:31])([F:30])[CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][C:17]2[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=2[O:27][CH3:28])[CH2:6][C:5]1=[O:29].CC(C)([O-])C.[K+].C(C1C=C(C(C)C)C=C(C(C)C)C=1S([N:56]=[N+:57]=[N-:58])(=O)=O)(C)C.C(=O)([O-])O.[Na+]>C1COCC1.C(O)(=O)C>[N:56]([CH:6]1[N:7]([CH2:16][C:17]2[C:18]([O:27][CH3:28])=[CH:19][C:20]([O:25][CH3:26])=[CH:21][C:22]=2[O:23][CH3:24])[C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:4]([CH2:3][C:2]([F:1])([F:30])[F:31])[C:5]1=[O:29])=[N+:57]=[N-:58]

Participants

Conditions

Temperature: -78 °C

Procedure

The product from Step 4C (1 g, 0.0023 mol) was dissolved in THF (30 ml) under nitrogen, cooled to −78° C. and potassium tert butoxide (0.28 g, 0.0025 mol) as a solution in THF (5 ml) added over 10 minutes. 2,4,6-Triisopropylbenzenesulfonyl azide (1.65 g, 0.005 mol) in THF (5 ml) was added dropwise and the mixture stirred for 10 minutes. Glacial acetic acid (0.6 ml) was added and the reaction mixture allowed to attain room temperature and left to stir for 4 hours. The reaction mixture was poured into sodium hydrogen carbonate solution and extracted (ethyl acetate ×2). The combined organic layers were washed (brine), dried (MgSO4) and evaporated in vacuo to give the desired azide which was used without further purification.

Workup

customto attain room temperature
waitleft
stirringto stir for 4 hours
extractionextracted (ethyl acetate ×2)
washThe combined organic layers were washed (brine)
dry with materialdried (MgSO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-57f35610585c41b38f0270a7fb4540bd
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105509B2

Reaction notes

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