{3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid benzyl ester → {3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid

HRID 343104

반응식

HRID 343104 반응식
[CH2:1]([O:8][C:9](=[O:56])[CH2:10][C:11]1([CH2:45][C:46]([O:48]CC2C=CC=CC=2)=[O:47])[C:17](=[O:18])[N:16]([C:19]([CH:31]([CH3:33])[CH3:32])([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:20](=[O:22])[NH2:21])[C:15]2[CH:34]=[CH:35][CH:36]=[CH:37][C:14]=2[N:13]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:12]1=[O:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH2:1]([O:8][C:9]([CH2:10][C:11]1([CH2:45][C:46]([OH:48])=[O:47])[C:17](=[O:18])[N:16]([C:19]([CH:31]([CH3:33])[CH3:32])([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:20](=[O:22])[NH2:21])[C:15]2[CH:34]=[CH:35][CH:36]=[CH:37][C:14]=2[N:13]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:12]1=[O:44])=[O:56])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 86753588{3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid benzyl ester

생성물 1

HCID 86753587{3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid수율 32.6%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

450 mg (0.6 mmols) of {3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid benzyl ester, prepared as in Intermediate 27, is dissolved in 100 mL of ethyl acetate and 45 mg of 10% Pd/C is added. The reaction mixture is then kept under a hydrogen atmosphere with stirring for 2.5 h. The solution is then filtered through celite and the solvent is removed in vacuo. The resulting white solid is purified by reverse phase MPLC in methanol/water 70/30 as eluent to afford 130 mg (32%) of the title compound as a white solid: 1H NMR (CDCl3, 300 MHz) δ7.38-6.54 (m, 18H), 5.29-4.88 (m, 4H), 4.23 (m, 1H), 3.83 (d, J=7.5, 3H), 3.23-2.69 (m, 4H), 1.08-1.02 (m, 6H); low resolution MS m/e 664.

후처리

  1. filtrationThe solution is then filtered through celite
  2. customthe solvent is removed in vacuo
  3. customThe resulting white solid is purified by reverse phase MPLC in methanol/water 70/30 as eluent

출처 및 근거

ORD 기록
ord-0190849fc4614cf5800ef73ea7104c43
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859007

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