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2-Tetralone → 2-(S)-(1,2,3,4-Tetrahydro-naphthalen-2-ylamino)-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide

HRID 131657
ノート
印刷プレビュー

反応式

HRID 131657 の反応式
[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:16])[C@@H:11]([NH2:15])[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][C:18]1=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:16])[C@@H:11]([NH:15][CH:23]2[CH2:24][CH2:25][C:26]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:22]2)[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 682662-TetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 866045872-(S)-amino-pentanoic acid (5-isopropyl-thiazol-2-yl)amide

生成物 1

HCID 116104112-(S)-(1,2,3,4-Tetrahydro-naphthalen-2-ylamino)-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒
HCID 6344
Dichloromethane
溶媒

実験手順

A mixture of 2-(S)-amino-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide (350 mg, 1.4 mmol) and 2-tetralone (318 mg, 2.2 mmol)in 20 mL of methylene chloride and 5 drops of acetic acid was treated with sodium triacetoxyborohydride (462 mg, 2.2 mmol) and stirred at room temperature overnight. The mixture was concentrated and eluted through SPEC SCX cartridge and concentrated to dryness. The residue was purified by silica gel column chromatography to give 2-(S)-(1,2,3,4-Tetrahydro-naphthalen-2-ylamino)-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide as a solid, LC-MS, RT=1.9 min, M+1=372.

後処理

  1. concentrationThe mixture was concentrated
  2. washeluted through SPEC SCX cartridge
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-e16c27bbe9224dc3992a6a93e3689b5c
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07384968B2

反応ノート

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