3-Heptanone → 2-(s)-(1-Propyl-butylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide

HRID 131656

反応式

HRID 131656 の反応式
Cl.C[O:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH2:21])[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9].[CH3:25][CH2:26][C:27](=O)[CH2:28][CH2:29][CH2:30][CH3:31].S([O-])([O-])(=O)=O.[Na+].[Na+].C([BH3-])#N.[Na+]>ClC(Cl)C.CO.C(O)(=O)C>[OH:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH:21][CH:28]([CH2:29][CH2:30][CH3:31])[CH2:27][CH2:26][CH3:25])[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9]

参加物

8

反応物 4

HCID 78023-HeptanoneHCID 24436Sodium SulfateHCID 5003444Sodium cyanoborohydrideHCID 1317269182-(S)-amino-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide HCl salt

生成物 1

HCID 116547832-(s)-(1-Propyl-butylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
40 °C

実験手順

A mixture of 2-(S)-amino-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide HCl salt (100 mg, 0.265 mmol) and 3-heptanone (0.1 mL), acetic acid (0.2 mL), sodium sulfate and sodium cyanoborohydride (100 mg) in dichloroethane (2 mL) and methanol (1 mL) was stirred at 40° C. overnight. The mixture was quenched with water, basified by dilute sodium hydroxide, and extracted with methylene chloride. The organic layer was concentrated to dryness. The residue was purified by Biotage silica gel column chromatography to isolate 2-(S)-(1-propyl-butylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide as a colorless oil, LC-MS, RT=2.2 min, M+1=426.5.

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with methylene chloride
  3. concentrationThe organic layer was concentrated to dryness
  4. customThe residue was purified by Biotage silica gel column chromatography

出典と根拠

ORDレコード
ord-59679df6d87c47658f1cf87b4a0d71bc
出典データセット
uspto-grants-2008_06
特許番号
US07384968B2

関連ノート

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