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Methylamine → (S)-benzyl (1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate

HRID 2202561
ノート
印刷プレビュー

反応式

HRID 2202561 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]1[O:22][C:23]([C:26]2[C:27]([O:36][CH3:37])=[N:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:24][N:25]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](O)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:38][N:39](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>CN(C=O)C.CCOC(C)=O>[CH3:37][O:36][C:27]1[C:26]([C:23]2[O:22][C:21]([C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:39][CH3:38])=[O:19])=[N:25][CH:24]=2)=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

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 90149568(S)-7-(((benzyloxy)carbonyl)amino)-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)heptanoic acid

生成物 1

HCID 90149176
(S)-benzyl (1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of F5 in DMF (0.1 M) were added HATU (2.0 eq.) and DIPEA (3.0 eq.) followed after 10 min by methylamine (2.0 M solution in THF, 5.0 eq.). Reaction mixture was stirred at room temperature for 16 h. Then, reaction mixture was diluted with EtOAc, washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude was purified by column chromatography (eluent: Petroleum ether/EtOAc from 1:1 to 100% EtOAc, then EtOAc/MeOH=95:5) to give the title compound as pale yellow solid. MS (ES+) C29H32N4O5: 517 (M+H)+.

後処理

  1. customReaction mixture
  2. customThen, reaction mixture
  3. washwashed with sat. aq. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude was purified by column chromatography (eluent

出典と根拠

ORDレコード
ord-e38efdc0bf05487090e6c2cee57928b7
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365541B2

反応ノート

読み込み中…

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