Trifluoroacetic acid → 2-Amino-3-(7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester

HRID 1177735노트

반응식

HRID 1177735 반응식
[CH3:1][O:2][C:3](=[O:32])[CH:4]([N:17](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[CH2:5][N:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[NH:14][N:15]=[CH:16][C:8]=2[CH2:7]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:32])[CH:4]([NH2:17])[CH2:5][N:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[NH:14][N:15]=[CH:16][C:8]=2[CH2:7]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 588644042-(Di-tert-butoxycarbonylamino)-3-(7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester

생성물 1

HCID 588644942-Amino-3-(7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester수율 94%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(di-tert-butoxycarbonylamino)-3-(7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester (0.49 g, 1 equiv) in methylene chloride (5 mL, 0° C.) was added trifluoroacetic acid (1.5 mL). The ice bath was removed and stirring continued for 2 h. The solution was concentrated, redissolved in methanol, and loaded onto a column of strong cation exchange resin. After flushing with methanol, the product was removed from the column by eluting with 2M ammonia in methanol to afford the product as its free base (250 mg, 94%). 1H-NMR (CDCl3, 500 MHz) δ 1.27 (s, 3H), 1.28 (s, 3H), 2.41 (d, J=11.3, 1H), 2.50 (d, J=11.3, 1H), 2.69 (dd, J=12.5, 7.9, 1H), 2.82 (dd, J=12.5, 5.2, 1H), 3.45 (d, J=12.8, 1H), 3.52 (d, J=12.8, 1H), 3.67 (m, 1H), 3.69 (s, 3H), 7.19 (s, 1H). Mass spec.: 253.16 (MH)+.

후처리

  1. customThe ice bath was removed
  2. concentrationThe solution was concentrated
  3. dissolutionredissolved in methanol
  4. customAfter flushing with methanol
  5. customthe product was removed from the column
  6. washby eluting with 2M ammonia in methanol

출처 및 근거

ORD 기록
ord-74e28c910c1143b4b23723079303ba35
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842808B2

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