Diisopropylethylamine → HCID 66899848、化合物

HRID 19043ノート

反応式

HRID 19043 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C@@H:14]([O:16][CH2:17][CH3:18])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[OH:20][C@@H:21]([CH2:51]O)[CH2:22][N:23]1[CH:27]=[CH:26][C:25]([NH:28]C(=O)[C@@H](N2CC(OC3C=CC=C(Cl)C=3Cl)=CC2=O)CC(C)C)=[N:24]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:63]=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:12])[NH:28][C:25]1[CH:26]=[CH:27][N:23]([CH2:22][C:21]([OH:20])([CH3:51])[CH3:63])[N:24]=1)[CH2:13][C@@H:14]([O:16][CH2:17][CH3:18])[CH3:15])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66899094HMS5552 HClHCID 86635230(2S,4S)-2-t-butoxycarbonylamino-4-ethoxy-pentanoic acid

生成物 1

HCID 66899848HCID 66899848、化合物収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(2S,4S)-2-t-butoxycarbonylamino-4-ethoxy-pentanoic acid (401 mg, 1.536 mmol) was mixed with 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (prepared in U.S. Pat. Appl. US2008021032 Example 80, 334 mg, 2.16 mmol) in N,N-dimethylformamide (10 mL). benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (1.23 g, 2.77 mmol) and N,N-diisopropylethylamine (0.7 mL) was added at 0° C. The mixture was stirred at room temperature overnight. Solvents were evaporated and the residue was extracted with ethyl acetate and saturated sodium chloride solution. The solvents were evaporated and the crude material was purified by flash column chromatography (silica gel, 10-80% ethyl acetate/hexanes) to afford {(1S,3S)-3-ethoxy-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-butyl}-carbamic acid t-butyl ester (486 mg, 80%) as a white solid: LR-ES-MS m/z calculated for C19H34N4O5 [M]+ 398, observed [M+H]+ 399.

後処理

  1. customSolvents were evaporated
  2. extractionthe residue was extracted with ethyl acetate and saturated sodium chloride solution
  3. customThe solvents were evaporated
  4. customthe crude material was purified by flash column chromatography (silica gel, 10-80% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-57aa69201bd24472ae91f3b3dcdc10d7
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

読み込み中…