Triethylamine → (2R)-2-[[4-(2-Bromo-acetylamino)-benzyl]-(4-chlorobenzenesulfonyl)-amino]-4-methyl-pentanoic acid amide

HRID 507322ノート

反応式

HRID 507322 の反応式
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C@H:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.CCN(CC)CC.[Br:35][CH2:36][C:37](Cl)=[O:38]>C(Cl)Cl>[Br:35][CH2:36][C:37]([NH:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)(=[O:18])=[O:17])[C@H:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1)=[O:38]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 59001017(2R)-2-[(4-aminobenzyl)-(4-chloro-benzenesulfonyl)amino]-4-methyl-pentanoic acid amide

生成物 1

HCID 10218145(2R)-2-[[4-(2-Bromo-acetylamino)-benzyl]-(4-chlorobenzenesulfonyl)-amino]-4-methyl-pentanoic acid amide収率 42%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (2R)-2-[(4-aminobenzyl)-(4-chloro-benzenesulfonyl)amino]-4-methyl-pentanoic acid amide (248 mg, 0.56 mmol) and Et3N (176 mg, 1.74 mmol) in CH2Cl2 (3 mL) was added bromoacetylchloride (105 mg, 0.67 mmol). The reaction mixture was stirred overnight at rt. The reaction mixture was diluted with CH2Cl2 (5 mL), washed with 1 N HCl, brine, and dried through a cotton plug. The solvent was removed in vacuo. Purification by flash chromatography (SiO2, 10% acetone/CH2Cl2) afforded the title compound (124 mg) in 42% yield. MS (ESI), (M+H)+ 531.86, 1H NMR (CDCl3, 400 MHz) δ 8.78 (br s, NH), 7.95 (d, 2H, J=8.0), 7.82 (d, 2H, J=8.0), 7.42 (d, 2H, J=8.0), 7.33 (d, 2H, J=8.0), 6.20 (br s, 1H), 5.20 (br s, 1H), 4.30 (s, 2H), 4.22 (d, 1H, Jab=16), 4.14 (d, 1H, Jab=16), 3.25 (t, 1H, J=6.0), 1.95 (m, 1H), 1.60 (m, 2H), 0.98 (d, 3H, J=7.0), 0.94 (d, 3H, J=7.0)

後処理

  1. washwashed with 1 N HCl, brine
  2. customdried through a cotton plug
  3. customThe solvent was removed in vacuo
  4. customPurification by flash chromatography (SiO2, 10% acetone/CH2Cl2)

出典と根拠

ORDレコード
ord-bb1a2d54637e4b6aa621b2dbaae4a715
出典データセット
uspto-grants-2010_08
特許番号
US07786122B2

反応ノート

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