Sodium hydride → HCID 15636920, compound

HRID 1769953Notes

Reaction equation

[N+](C1C=CC([C:10]2[C:18]([CH2:19][C@H:20]3[C@@H:25]([OH:26])[C:24]4[CH:27]=[C:28]([O:31][CH2:32][C:33]5[S:34][C:35]6[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:36]=6[N:37]=5)[CH:29]=[CH:30][C:23]=4[O:22][CH2:21]3)=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([O-])=[O:13])=CC=1)([O-])=O.[H-].[Na+].[CH3:45][S:46]([NH2:49])(=[O:48])=[O:47]>>[F:42][C:39]1[CH:40]=[CH:41][C:35]2[S:34][C:33]([CH2:32][O:31][C:28]3[CH:29]=[CH:30][C:23]4[O:22][CH2:21][C@@H:20]([CH2:19][C:18]5[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=5)[C:12]([NH:49][S:46]([CH3:45])(=[O:48])=[O:47])=[O:13])[C@@H:25]([OH:26])[C:24]=4[CH:27]=3)=[N:37][C:36]=2[CH:38]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 72879Methanesulfonamide

HCID 67704692HCID 67704692, compound

Product 1

HCID 15636920HCID 15636920, compound

Procedure

Synthesis was carried out as in example 1, but using 1.7 grams optically pure (+)cis-4-nitrophenyl-3-[[6-[(5-fluoro-2-benzothiazolyl)methoxy]-3,4-dihydro -4-hydroxy-2H-1-benzopyran-3-yl]methyl]benzoate, 410 milligrams sodium hydride and 1.65 grams methanesulfonamide. 187 milligrams of product was obtained. αD =33.4°; c=0.005 in tetrahydrofuran.

Workup

customSynthesis

Sources & evidence

ORD record: ord-f7ed2b912b5d4bfab687da8d25fb5f3a
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05384318

Reaction notes

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