Trifluoroacetic acid → Racemic 4-{[(3S,4R)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

HRID 15359ノート

反応式

HRID 15359 の反応式
CC([N:5]([C@@H:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[C:20]3=[C:21]([F:29])[CH:22]=[N:23][C:24]4[CH:25]=[CH:26][C:27](=[O:28])[N:18]([C:19]=43)[CH2:17]2)[CH2:11][C@@H:10]1[OH:30])C(=O)[O-])(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:5][C@@H:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[C:20]3=[C:21]([F:29])[CH:22]=[N:23][C:24]4[CH:25]=[CH:26][C:27](=[O:28])[N:18]([C:19]=43)[CH2:17]2)[CH2:11][C@@H:10]1[OH:30]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 131728174HCID 131728174、化合物

生成物 1

HCID 68684481Racemic 4-{[(3S,4R)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of racemic 1,1-dimethylethyl{(3S,4R)-1-[(3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-3-hydroxy-4-piperidinyl}carbamate (15.57 g) in dichloromethane (170 ml) was cooled in ice-water, treated with trifluoracetic acid (137 ml), stirred 1 hour at room temperature and evaporated to dryness. After keeping under high vacuum for 1 hour, the crude material was dissolved in methanol and run through a column of Amberlyst A21 basic resin (500 ml) (Sigma-Aldrich Co.), eluting with methanol. The solution containing the product was evaporated and the residue chromatographed on silica gel, eluting with dichloromethane/methanol/0.88 ammonia (9:1:0.1) to give product (8.96 g, 76%).

後処理

  1. customevaporated to dryness
  2. waitAfter keeping under high vacuum for 1 hour
  3. dissolutionthe crude material was dissolved in methanol
  4. washeluting with methanol
  5. additionThe solution containing the product
  6. customwas evaporated
  7. customthe residue chromatographed on silica gel
  8. washeluting with dichloromethane/methanol/0.88 ammonia (9:1:0.1)

出典と根拠

ORDレコード
ord-5227c8331d0b4dce93bf2739e19ce181
出典データセット
uspto-grants-2010_06
特許番号
US07732461B2

反応ノート

読み込み中…