Sodium triacetoxyborohydride → Hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-({9-[(R)-2-(tert-butyldimethyl-silanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]nonyl}methyl-amino)bicyclo[2.2.1]hept-2-yl ester

HRID 1670900노트

반응식

HRID 1670900 반응식
[CH3:1][N:2]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=O)[C@H:3]1[C@H:7]2[CH2:8][CH2:9][C@@H:4]1[C@H:5]([O:10][C:11](=[O:24])[C:12]([OH:23])([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[CH2:6]2.[NH2:35][CH2:36][C@@H:37]([C:46]1[CH:55]=[CH:54][C:53]([OH:56])=[C:52]2[C:47]=1[CH:48]=[CH:49][C:50](=[O:57])[NH:51]2)[O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCCl>[C:42]([Si:39]([CH3:41])([CH3:40])[O:38][C@H:37]([C:46]1[CH:55]=[CH:54][C:53]([OH:56])=[C:52]2[C:47]=1[CH:48]=[CH:49][C:50](=[O:57])[NH:51]2)[CH2:36][NH:35][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:2]([CH3:1])[C@H:3]1[C@H:7]2[CH2:8][CH2:9][C@@H:4]1[C@H:5]([O:10][C:11](=[O:24])[C:12]([OH:23])([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[CH2:6]2)([CH3:45])([CH3:44])[CH3:43]

참가 물질

6

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-oneHCID 86642393hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-[methyl-(9-oxo-nonyl)amino]bicyclo[2.2.1]hept-2-yl ester

생성물 1

HCID 67350381Hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-({9-[(R)-2-(tert-butyldimethyl-silanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]nonyl}methyl-amino)bicyclo[2.2.1]hept-2-yl ester

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 111,2-Dichloroethane용매

실험 절차

A mixture of hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-[methyl-(9-oxo-nonyl)amino]bicyclo[2.2.1]hept-2-yl ester (max 0.73 mmol), 5-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-8-hydroxy-1H-quinolin-2-one (245 mg, 0.73 mmol), sodium triacetoxyborohydride (186 mg, 0.88 mmol), and acetic acid (2 drops) in dry 1,2-dichloroethane was stirred at ambient temperature overnight. The reaction mixture was partitioned between DCM and satd NaHCO3 (aq). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to afford a dark green/brown gum that solidified on standing, which was purified by preparative HPLC (system 2, 35% B+1% B/min). The fractions containing pure product were concentrated, neutralised with satd NaHCO3 (aq), and extracted with DCM. After concentration in vacuo a green/brown oil was obtained.

후처리

  1. customThe reaction mixture was partitioned between DCM and satd NaHCO3 (aq)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford a dark green/brown gum that
  6. customwas purified by preparative HPLC (system 2, 35% B+1% B/min)
  7. additionThe fractions containing pure product
  8. concentrationwere concentrated
  9. extractionextracted with DCM
  10. concentrationAfter concentration in vacuo a green/brown oil
  11. customwas obtained

출처 및 근거

ORD 기록
ord-ce9824fd5b8b48ad92f485b7fcc98d1e
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994211B2

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