Lithium Hydroxide → 4-{[(1-tert-Butoxycarbonyl-2-methyl-propyl)-(4-methoxy-benzenesulfonyl)-amino]-methyl}-benzoic acid

HRID 1517168ノート

反応式

HRID 1517168 の反応式
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:24]([CH3:26])[CH3:25])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:6][CH:5]=1.[Li+].[OH-]>O1CCCC1>[C:30]([O:29][C:27]([CH:23]([N:11]([CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:34])=[O:2])=[CH:9][CH:8]=1)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:24]([CH3:26])[CH3:25])=[O:28])([CH3:32])([CH3:33])[CH3:31]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 694513514-{[(1-tert-Butoxycarbonyl-2-methyl-propyl)-(4-methoxy-benzenesulfonyl)-amino]-methyl}benzoic acid methyl ester

生成物 1

HCID 694468364-{[(1-tert-Butoxycarbonyl-2-methyl-propyl)-(4-methoxy-benzenesulfonyl)-amino]-methyl}-benzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

The diester (Compound 7*) (151 mg, 0.31 mmol) was dissolved in tetrahydrofuran (2 ml) and 4N LiOH (250 μl) was added at ambient temperature. The mixture was heated to 60° C. for 5 hours when HPLC monitoring showed the hydrolysis was completed. The mixture was cooled to ambient temperature and the solvent was evaporated. The residue was dissolved in water and the clear solution extracted with once with diethyl ether. Then the aqueous phase was cooled to 5° C. (ice/water) and neutralised with 1N HCl and after which it was extracted with ethyl acetate (3×5 ml). The combined ethyl acetate phases was extracted with water (5 ml) and brine (5 ml), dried with (Na2SO4), filtered and evaporated to afford the product as white foam. Yield 133 mg (90%).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in water
  4. extractionthe clear solution extracted with once with diethyl ether
  5. temperatureThen the aqueous phase was cooled to 5° C. (ice/water)
  6. extractionafter which it was extracted with ethyl acetate (3×5 ml)
  7. extractionThe combined ethyl acetate phases was extracted with water (5 ml) and brine (5 ml)
  8. dry with materialdried with (Na2SO4)
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-7f122147ac71481a9ff85223b417ae98
出典データセット
uspto-grants-2012_07
特許番号
US08231858B2

反応ノート

読み込み中…