Ammonium Hydroxide → 5-[4''-(3-Benzyloxy-5-butyl-[1,2,4]triazol-4-ylmethyl)-biphenyl-2-yl]-1H-tetrazole

HRID 1742113노트

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HRID 1742113 반응식
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8](S(C)(=O)=O)=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:32]([O:39]CC1C=CC=CC=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Na].[Na].[NH4+].[OH-]>C(O)C1C=CC=CC=1>[CH2:32]([O:39][C:8]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][N:7]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

6

반응물 4

HCID 14923Ammonium HydroxideHCID 5360545SodiumHCID 66729449CID 66729449HCID 1784419605-[4''-(3-Butyl-5-methanesulfonyl-[1,2,4]triazol-4-ylmethyl)-biphenyl-2-yl]-1H-tetrazole

생성물 1

HCID 1784419535-[4''-(3-Benzyloxy-5-butyl-[1,2,4]triazol-4-ylmethyl)-biphenyl-2-yl]-1H-tetrazole수율 12%

시약·촉매·용매 1

HCID 244Benzyl Alcohol용매2회

실험 절차

A solution of 35 mg (0.08 mmole) of 3-n-butyl-5-methylsulfonyl-4-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-4M-1,2,4-triazole (from Example 24) in 300 μl (0.21 mmole) of 0.71 M sodium benzyloxide in benzyl alcohol (freshly prepared from sodium and benzyl alcohol) was stirred at 60° C. for 20 hours, by which time TLC (90:10:1CH2Cl2 --MeOH-concd. NH4OH, developed 3×) indicated complete reaction. The mixture was partitioned between 20 ml of ethyl acetate and 15 ml of 0.2 N HCl. The organic phase was washed with 2×10 ml of 0.2 N HCl, then dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution with 19:1 and then 9:1CH2Cl2 --MeOH). Concentration of clean product fractions yielded 4.4 mg (12%) of the title compound as a residual glass, homogeneous by TLC in 90:10:1 CH2Cl2 --MeOH-concd. NH4OH; mass spectrum (FAB) m/e 466 (M+1)+.

후처리

  1. customreaction
  2. customThe mixture was partitioned between 20 ml of ethyl acetate and 15 ml of 0.2 N HCl
  3. washThe organic phase was washed with 2×10 ml of 0.2 N HCl
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (
  8. washelution with 19:1

출처 및 근거

ORD 기록
ord-c143fb1c897c4ce6b266559a82f1f03f
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05336778

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