Hydrochloric Acid → HCID 67353694、化合物

HRID 75818ノート

反応式

HRID 75818 の反応式
C[O:2][C:3](=[O:33])[CH:4]([NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])=[O:24])=[CH:18][CH:17]=2)[CH:12]=1)=[O:10])[CH:5]([CH3:7])[CH3:6].[Li+].[OH-].Cl>C1COCC1>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][C:23](=[O:24])[NH:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:12]=[C:11]([C:9]([NH:8][CH:4]([CH:5]([CH3:6])[CH3:7])[C:3]([OH:33])=[O:2])=[O:10])[O:15][N:14]=2)=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 673524222-[(3-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid methyl ester

生成物 1

HCID 67353694HCID 67353694、化合物収率 63.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-[(3-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid methyl ester (800 mg) was dissolved in THF (20 ml). 1M aqueous LiOH solution (3.52 ml) was added and stirred at RT for 14 h. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to get off white solid which was crystallized from EtOAc to yield 490 mg (63%) white solid. MS (ES+): m/z 441 (M+1); 1HNMR (DMSO-d6, 300 MHz): δ 12.83 (bs, 1H), 9.34 (s, 1H), 8.95 (d, 1H), 8.63 (s, 1H), 8.13 (m, 1H), 7.85 (d, 2H), 7.68 (s, 1H), 7.62 (d, 2H), 7.24 (m, 1H), 7.14 (m, 1H), 7.02 (m, 1H), 4.26 (m, 1H), 2.21 (m, 1H), 0.95 (dd, 6H).

後処理

  1. extractionextracted with EtOAc
  2. customOrganic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get off white solid which
  6. customwas crystallized from EtOAc

出典と根拠

ORDレコード
ord-e01872e5c2c04eb2b140933f6eb132e3
出典データセット
uspto-grants-2014_09
特許番号
US08835428B2

反応ノート

読み込み中…