Diisopropylethylamine → HCID 178503634、化合物

HRID 2216157ノート

反応式

HRID 2216157 の反応式
[C:1]([NH:4][C@H:5]([C:10]([OH:12])=[O:11])[C:6]([SH:9])([CH3:8])[CH3:7])(=[O:3])[CH3:2].[CH3:13]CN(C(C)C)C(C)C.[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25].BrC[C:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[C:35]=1[C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([S:47]([C:50]2[CH:54]=[C:53]([C:55](=[NH:57])[NH2:56])[S:52][C:51]=2[S:58][CH3:59])(=[O:49])=[O:48])[CH:42]=1)=[O:32]>CS(C)=O>[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25].[C:1]([NH:4][CH:5]([C:6]([SH:9]([C:31](=[O:32])[NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[C:35]=1[C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([S:47]([C:50]2[CH:54]=[C:53]([C:55](=[NH:56])[NH2:57])[S:52][C:51]=2[S:58][CH3:59])(=[O:49])=[O:48])[CH:42]=1)[CH3:13])([CH3:7])[CH3:8])[C:10]([OH:12])=[O:11])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 164975N-acetylpenicillamine, (L)-HCID 218861962-Bromo-N-[3'-(5-carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-acetamide trifluoroacetate

生成物 1

HCID 178503634HCID 178503634、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

N-Acetyl-penicillamine (3.0 mg, 0.0154 mmol, racemic) and DIEA (7 μL, 0.04 mmol) were dissolved in DMSO (223 μL) and then transferred to a solution of 2-bromo-N-[3′-(5-carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-acetamide trifluoroacetate (20 mM in DMSO, 230 μL, 0.0046 mmol, prepared from the title compound described in Example 249). The reaction was mixed on a shaker for 1 h at rt. Bromomethyl wang resin (16 mg, 1.47 mmol/gm) was added to scavenge the excess thiol. After 2 h of shaking, the resin was filtered and the filtrate was directly purified using RP-HPLC as previously described in Example 246, step b, to afford 1.5 mg (50%, single peak on analytical RP-HPLC) of the title compound as a glassy solid. ESI-MS (m/z): Calcd. for C28H32N4O6S4: 649.1 (M+H); found: 649.1.

出典と根拠

ORDレコード
ord-6fe065d99d4f4ec181f7fb9e2118fc17
出典データセット
uspto-grants-2006_09
特許番号
US07109354B2

反応ノート

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