N,O-bis(trimethylsilyl)acetamide → 2-(2-Hydroxyethyl)-5-[4-(2-phenylbenzoylamino)-benzenesulfonyl]-1,5-benzothiazepine

HRID 2296757Notes

Reaction equation

HRID 2296757 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH:10]=[CH:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=2[S:5]1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[C:37]1([C:43]2[CH:51]=[CH:50][CH:49]=[CH:48][C:44]=2[C:45](Cl)=[O:46])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[OH:1][CH2:2][CH2:3][CH:4]1[CH:10]=[CH:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:45](=[O:46])[C:44]3[CH:48]=[CH:49][CH:50]=[CH:51][C:43]=3[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=2[S:5]1

Participants

4

Reactant 3

HCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 183874372-(2-Hydroxyethyl)-5-(4-aminobenzenesulfonyl)-1,5-benzothiazepine

Product 1

HCID 183874492-(2-Hydroxyethyl)-5-[4-(2-phenylbenzoylamino)-benzenesulfonyl]-1,5-benzothiazepine

Procedure

Compound 4 as prepared in Example 25 (0.6 g, 1.5 mM) was treated with N,O-bis(trimethylsilyl)acetamide (0.65 g, 3.0 ml) then with 2-phenylbenzoyl chloride (0.39 g,1.8 mM) as described in Example 22 to yield the title product as a white solid. m.p. 1H NMR (300 MHz, CDCl3) δ7.92 (d, J=7.4 Hz, 1H); 7.60-7.04 (m, 17H); 3.76 (m, 2H); 2.89 (m, 1H); 2.08 (m, 1H); 1.90 (m, 1H); 1.64 (m, 4H). m/z (MH+)545

Sources & evidence

ORD record
ord-2ee54cd177244f9e8b21a67ef9e0f45e
Source dataset
uspto-grants-2002_12
Patent number
US06489321B1

Reaction notes

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