Diisopropylethylamine → (2S,3S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737209노트

반응식

HRID 737209 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([OH:16])[C@H:12]1[C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O.[NH2:60][C:61]1[S:62][CH:63]=[C:64]([C:66]2[CH:77]=[CH:76][C:69]([C:70]([NH:72][CH:73]3[CH2:75][CH2:74]3)=[O:71])=[CH:68][CH:67]=2)[N:65]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([OH:16])[C@H:12]1[C:17](=[O:19])[NH:60][C:61]1[S:62][CH:63]=[C:64]([C:66]2[CH:67]=[CH:68][C:69]([C:70](=[O:71])[NH:72][CH:73]3[CH2:75][CH2:74]3)=[CH:76][CH:77]=2)[N:65]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54213972(2S,3S)-1-[(benzyloxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acidHCID 866164294-(2-Amino-thiazol-4-yl)-n-cyclopropyl-benzamide trifluoroacetic acid salt

생성물 1

HCID 57849874(2S,3S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(2S,3S)-3-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (41.9 mg, 1.6 mmol) and HATU (66.3 mg, 1.7 mmol) were dissolved in DMF (2 mL). DIEA (55 μL, 0.32 mmol) was then added, and the reaction was stirred at ambient temperature for 15 minutes. Then 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide trifluoroacetic acid salt (62.9 mg, 0.17 mmol) was added, and the reaction was stirred at ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product. Yield 11.8 mg. MS: 507.2 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 0.50-77 (m, 4H), 1.70-2.10 (m, 2H), 4.20-4.40 (m, 1H), 4.86-5.17 (m, 2H), 7.00-7.42 (m, 4H), 7.74-8.01 (m, 5H), 8.40-8.48 (m, 1H), 12.58-12.67 (m, 1H).

후처리

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. filtrationThe reaction was filtered
  3. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-45d663fe358d4192bd8f752b7fe15eb9
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595398B2

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