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

HRID 737209ノート

反応式

HRID 737209 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(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).

後処理

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

出典と根拠

ORDレコード
ord-45d663fe358d4192bd8f752b7fe15eb9
出典データセット
uspto-grants-2009_09
特許番号
US07595398B2

反応ノート

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