1-(4-Amino-quinazolin-7-ylmethyl)-4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one → 1-(4-Amino-quinazolin-7-ylmethyl)-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one

HRID 1433060ノート

反応式

HRID 1433060 の反応式
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16](C(OCC4C=CC=CC=4)=O)[C@@H:15]([CH2:29][CH2:30][S:31][CH3:32])[C:14]3=[O:33])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1>Br.C(O)(=O)C.CCOCC>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][NH:16][C@@H:15]([CH2:29][CH2:30][S:31][CH3:32])[C:14]3=[O:33])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

参加物

5

反応物 1

HCID 690288501-(4-Amino-quinazolin-7-ylmethyl)-4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one

生成物 1

HCID 670141251-(4-Amino-quinazolin-7-ylmethyl)-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one収率 42%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 260Hydrogen Bromide溶媒HCID 3283Diethyl Ether溶媒

実験手順

1-(4-Amino-quinazolin-7-ylmethyl)-4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one (100 mg, 0.215 mmol) is dissolved in 5 ml of 30% hydrogen bromide in acetic acid. The mixture is stirred for 1 hour, diluted with ethyle ether. The ether is decanted and the resulting solid is washed thoroughly with ethyle ether. The resulting crude product is purified by column chromatography eluting with a 4/2/1 mixture of CH2Cl2/MeOH/NH4OH (30% in H2O). with a gradient of 5% MeOH:CH2Cl2 to 10% MeOH:CH2Cl2. The resulting product is purified by another column chromatography eluting with a gradient of 20% MeOH:CH2Cl2 to 50% MeOH:CH2Cl2. The title bound (30 mg, 42% yield) is obtained as an off-white solid.

後処理

  1. customThe ether is decanted
  2. washthe resulting solid is washed thoroughly with ethyle ether
  3. customThe resulting crude product is purified by column chromatography
  4. washeluting with a 4/2/1 mixture of CH2Cl2/MeOH/NH4OH (30% in H2O)
  5. customThe resulting product is purified by another column chromatography
  6. washeluting with a gradient of 20% MeOH
  7. customis obtained as an off-white solid

出典と根拠

ORDレコード
ord-dd90b56c3fbe4e41b3c761cc6d155dbc
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

読み込み中…