Methylamine → HCID 86670469、化合物

HRID 1911853ノート

反応式

HRID 1911853 の反応式
CN.[C:3]([O:7][C:8]([N:10]1[C@@H:14]([C@H:15]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][CH2:12][C@H:11]1[CH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:40][N:41](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.C1COCC1>[Si:23]([O:22][C@H:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:14]1[CH2:13][CH2:12][C@@H:11]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:35](=[O:36])[NH:41][CH3:40])=[CH:38][CH:39]=2)[N:10]1[C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])([C:26]([CH3:28])([CH3:29])[CH3:27])([CH3:24])[CH3:25]

参加物

8

反応物 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67971935HCID 67971935、化合物

生成物 1

HCID 86670469HCID 86670469、化合物収率 59%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Methylamine (5.71 mL of a 2M THF solution, 11.4 mmol) was added to a stirred, room temperature solution of 4-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)benzoic acid (2.00 g, 3.80 mmol), HATU (1.736 g, 4.56 mmol, 1.2 equivalents) and DIPEA (3.32 mL, 19.0 mmol, 5 equivalents) in DMF (7.8 mL). The reaction was stirred at room temperature for 12 hours, after which the mixture was diluted with EtOAc and partitioned with water. The aqueous layer was extracted with EtOAc (3×), and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by normal phase flash chromatography using silica gel (0-50% hexanes/ethyl acetate). The product fractions were collected and concentrated in vacuo to afford the title compound as a white solid (1.20 g, 59%). LC-MS=561.2 (M+Na)+.

後処理

  1. custompartitioned with water
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by normal phase flash chromatography
  8. customThe product fractions were collected
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-484b98469d50470895a1e58bba4d9704
出典データセット
uspto-grants-2013_12
特許番号
US08604038B2

反応ノート

読み込み中…