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

HRID 131656

반응식

HRID 131656 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 63651,1-Dichloroethane용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-59679df6d87c47658f1cf87b4a0d71bc
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384968B2

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