1,2-Dichloroethane → n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-carboxamide

HRID 228082ノート

反応式

HRID 228082 の反応式
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)(=[O:5])=[O:4].[CH3:19][C:20]([O:23][C:24]([NH:26][C@@H:27]([C:37]([OH:39])=[O:38])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1)=[O:25])([CH3:22])[CH3:21].CC[N:42]([CH:46]([CH3:48])C)[CH:43]([CH3:45])C.C(Cl)CCl.[CH:53]1[CH:58]=N[C:56]2N(O)N=N[C:55]=2[CH:54]=1>CN(C=O)C>[Cl:36][C:31]1[CH:30]=[C:29]([CH2:28][C@@H:27]([NH:26][C:24]([O:23][C:20]([CH3:22])([CH3:21])[CH3:19])=[O:25])[C:37]([N:16]2[CH2:17][CH2:18][N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[NH:6][S:3]([CH3:2])(=[O:4])=[O:5])[CH2:14][CH2:15]2)=[O:38])[CH:34]=[CH:33][C:32]=1[Cl:35].[Cl:36][C:31]1[CH:30]=[C:29]([CH2:28][C@@H:27]([NH:26][C:24]([C@@H:46]2[CH2:48][C:56]3[C:45](=[CH:58][CH:53]=[CH:54][CH:55]=3)[CH2:43][NH:42]2)=[O:25])[C:37]([N:16]2[CH2:17][CH2:18][N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[NH:6][S:3]([CH3:2])(=[O:4])=[O:5])[CH2:14][CH2:15]2)=[O:39])[CH:34]=[CH:33][C:32]=1[Cl:35]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 70158113,4-Dichloro-N-((1,1-dimethylethoxy)carbonyl)-D-phenylalanineHCID 21283546N-(2-(Piperazin-1-yl)phenyl)methanesulfonamide hydrochloride

生成物 2

HCID 10282776n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-carboxamide収率 113.3%HCID 21060073n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-[(1R)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide was prepared according to the procedure for Preparation XIX using (methylsulfonyl)(2-piperazinylphenyl)amine hydrochloride (800 mg, 2.8 mmol), N-Boc-D-3,4-dichlorophenylalanine (930 mg, 2.80 mmol) (Peptech), DIEA (480 μl, 2.80 mmol), EDC (1.66 g, 5.60 mmol), HOAT (400 mg, 3.0 mmol) and DMF (10 mL). The crude product was purified by flash chromatography (SiO2, 1:1 hexane:EtOAc) and concentrated in vacuo to afford the desired compound (1.0 g). MS (ESI, pos. ion) m/z: 571 (M+H), (ESI, neg. ion) m/z: 569 (M−H). Calc'd for C25H32Cl2N4O5S: 570.15.

後処理

  1. customThe crude product was purified by flash chromatography (SiO2, 1:1 hexane:EtOAc)
  2. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-965145ba56bd43d9bbff5519d303565f
出典データセット
uspto-grants-2009_07
特許番号
US07560460B2

反応ノート

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