(2S)-1-(4-nitrophenyl)sulfonylpyrrolidine-2-carboxylic acid → trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-(N-4-nitrobenzenesulfonyl-L-prolyloxy)-2H-1-benzopyran

HRID 327503ノート

反応式

HRID 327503 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:20][CH2:19][CH2:18][C@H:14]2[C:15]([OH:17])=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:21][C@H:22]1[C@H:27](O)[C:26]2[CH:29]=[C:30]([C:33]#[N:34])[CH:31]=[CH:32][C:25]=2[O:24][C:23]1([CH3:36])[CH3:35]>C(Cl)(Cl)Cl>[Br:21][C@H:22]1[C@H:27]([O:16][C:15](=[O:17])[C@@H:14]2[CH2:18][CH2:19][CH2:20][N:13]2[S:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)(=[O:11])=[O:12])[C:26]2[CH:29]=[C:30]([C:33]#[N:34])[CH:31]=[CH:32][C:25]=2[O:24][C:23]1([CH3:36])[CH3:35]

参加物

4

反応物 2

HCID 721326(2S)-1-(4-nitrophenyl)sulfonylpyrrolidine-2-carboxylic acidHCID 6932483trans-2,2-Dimethyl-3-bromo-6-cyanochroman-4-ol

生成物 1

HCID 86746457trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-(N-4-nitrobenzenesulfonyl-L-prolyloxy)-2H-1-benzopyran収率 41.4%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A similar procedure as in Example 1(1) was performed by using 6.7 g of N-4-nitrobenzenesulfonyl-L-proline and 5.7 g of (±)-trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol to give 4.72 g of trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-(N-4-nitrobenzenesulfonyl-L-prolyloxy)-2H-1-benzopyran as a sparingly soluble diastereomer compound, melting at 226.5°-227° C. with decomposition, [α]23D =+44.7° (c=1, CHCl3) and 5.01 g of the corresponding readily soluble diastereomer compound, melting at 177°-180° C., [α]23D =-93.2° (c=1, CHCl3), respectively.

出典と根拠

ORDレコード
ord-eb9df4690f584eb1a9813bdc1277ffa5
出典データセット
uspto-grants-1993_12
特許番号
US05273998

反応ノート

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