Triethylamine → HCID 67704729, compound

HRID 1769956Notes

Reaction equation

[CH2:1]([N:3](CC)[CH2:4]C)C.[N+](C1C=CC([C:17]2[C:25]([CH2:26][C@H:27]3[C@@H:32]([OH:33])[C:31]4[CH:34]=[C:35]([O:38][CH2:39][C:40]5[S:41][C:42]6[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:43]=6[N:44]=5)[CH:36]=[CH:37][C:30]=4[O:29][CH2:28]3)=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([O-])=[O:20])=CC=1)([O-])=O.C(OC(Cl)=O)C(C)C>O1CCCC1>[F:49][C:46]1[CH:47]=[CH:48][C:42]2[S:41][C:40]([CH2:39][O:38][C:35]3[CH:36]=[CH:37][C:30]4[O:29][CH2:28][C@@H:27]([CH2:26][C:25]5[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=5)[C:19]([N:3]([CH3:4])[CH3:1])=[O:20])[C@@H:32]([OH:33])[C:31]=4[CH:34]=3)=[N:44][C:43]=2[CH:45]=1

Participants

Conditions

Temperature: 0 °C

Procedure

364 milligrams triethylamine was added to a solution containing 1.5 grams cis-4-nitrophenyl-3-[[6-[(5-fluoro-2-benzothiazolyl)methoxy]-3,4-dihydro-4-hydroxy-2H-1-benzopyran-3-yl]methyl]benzoate in tetrahydrofuran at 0° C. After stirring for 5 minutes at 0° C., a solution of isobutylchloroformate in 5 milliliters of tetrahydrofuran was added dropwise. After stirring at 1° C. for 15 minutes, 364 milligrams anhydrous dimethylamine was bubbled into the reaction mixture for 1-2 minutes. The reaction mixture was allowed to warm to room temperature and the volatiles were evaporated. The residue was purified by chromatography on silica gel eluting with methylene dichloride/ethyl acetate to give 535 mg of product.

Workup

stirringAfter stirring at 1° C. for 15 minutes
custom364 milligrams anhydrous dimethylamine was bubbled into the reaction mixture for 1-2 minutes
temperatureto warm to room temperature
customthe volatiles were evaporated
customThe residue was purified by chromatography on silica gel eluting with methylene dichloride/ethyl acetate

Sources & evidence

ORD record: ord-cd5b94b6a20f47f5aa2a83c780cffcad
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05384318

Reaction notes

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