Water → trans-7-Chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid pivaloyloxymethyl ester

HRID 1771

반응식

HRID 1771 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:10](=[O:16])[C@@H:9]([CH2:17][C:18]([OH:20])=[O:19])[O:8][C@H:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:6]=2[CH:28]=1.[C:29]([O:35][CH2:36]Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].C(N(CC)CC(C)C)C(C)C.O>CN(C)C=O.C(OCC)(=O)C>[C:29]([O:35][CH2:36][O:19][C:18](=[O:20])[CH2:17][C@H:9]1[O:8][C@H:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[C:6]2[CH:28]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[C:10]1=[O:16])(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]

참가 물질

7

반응물 4

HCID 962WaterHCID 87885Chloromethyl pivalateHCID 12446309N-Ethyl-2-methyl-N-(2-methylpropyl)propan-1-amineHCID 22883210trans-7-Chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

생성물 1

HCID 67603055trans-7-Chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid pivaloyloxymethyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

In N,N-dimethylformamide (10 ml) was dissolved trans- 7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (0.5 g) obtained in Example 2. To the solution were added pivaloyloxymethyl chloride (0.43 ml), N,N-diisobutyl ethylamine (0.52 ml) and KI (0.2 g). The mixture was stirred at room temperature overnight. To the reaction mixture were added water (100 ml) and ethyl acetate (100 ml), followed by extraction. The ethyl acetate layer was washed with an aqueous solution of potassium hydrogensulfate, an aqueous solution of sodium hydrogencarbonate and water, successively, which was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to afford trans-7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid pivaloyloxymethyl ester (0.55 g).

후처리

  1. extractionfollowed by extraction
  2. washThe ethyl acetate layer was washed with an aqueous solution of potassium hydrogensulfate
  3. dry with materialan aqueous solution of sodium hydrogencarbonate and water, successively, which was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

출처 및 근거

ORD 기록
ord-157fb9c3937847cf98e7bf4bb5a1bfb6
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726306

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