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 15359노트

반응식

HRID 15359 반응식
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]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 131728174HCID 131728174, 화합물

생성물 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-one수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-5227c8331d0b4dce93bf2739e19ce181
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732461B2

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