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

HRID 987297노트

반응식

HRID 987297 반응식
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]

참가 물질

4

반응물 2

HCID 15891Phenyl chloroformateHCID 86595066HCID 86595066, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-eae89079890c4c9791886c40b1c8d63d
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630600B1

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