Phenyl chloroformate → (S)-2-ethoxy-3-(4-{2-[4-(phenoxycarbonylamino)phenyl]ethoxy]phenyl)propanoic acid ethyl ester

HRID 987297ノート

反応式

HRID 987297 の反応式
Cl.[CH2:2]([O:4][C:5](=[O:27])[C@@H:6]([O:24][CH2:25][CH3:26])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[CH:10][CH:9]=1)[CH3:3].Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>O1CCCC1>[CH2:2]([O:4][C:5](=[O:27])[C@@H:6]([O:24][CH2:25][CH3:26])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:29]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:30])=[CH:21][CH:22]=2)=[CH:10][CH:9]=1)[CH3:3]

参加物

4

反応物 2

HCID 15891Phenyl chloroformateHCID 86595066HCID 86595066、化合物

生成物 1

HCID 53791640(S)-2-ethoxy-3-(4-{2-[4-(phenoxycarbonylamino)phenyl]ethoxy]phenyl)propanoic acid ethyl ester収率 96.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester hydro chloride (described in Example 41b) (0.55 g; 1.4 mmole) was dissolved in tetrahydrofuran (5 ml). Phenyl chloroformat (0.675 g; 3 mmole) was added slowly. The reaction mixture was stirred at room temperature and continuosly checked with HPLC and after 3 days was all the starting material consumed. Water was added, tetrahydrofuran evaporated and the residue extracted three times with ethyl acetate. The organic phase was dried with magnesium sulfate and evaporated. Purification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm) using acetronitrile (70%) in ammonium acetate buffer (pH 7) as mobil phase gave 0.46 g (96.3% yield) (S)-2-ethoxy-3-(4-{2-[4-(phenoxycarbonylamino)phenyl]ethoxy]phenyl)propanoic acid ethyl ester.

後処理

  1. customconsumed
  2. additionWater was added
  3. customtetrahydrofuran evaporated
  4. extractionthe residue extracted three times with ethyl acetate
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. customevaporated
  7. customPurification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm)

出典と根拠

ORDレコード
ord-eae89079890c4c9791886c40b1c8d63d
出典データセット
uspto-grants-2003_10
特許番号
US06630600B1

反応ノート

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