Borohydride → Ethyl(4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)acetate

HRID 1171434노트

반응식

HRID 1171434 반응식
[CH2:1]([O:8][C:9]1[CH:28]=[C:27](I)[CH:26]=[CH:25][C:10]=1[CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:30]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[N:41]([CH3:46])[C:42]([SH:45])=[N:43][N:44]=2)=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31].[BH4-]>O1CCCC1.C(O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][CH2:11][C:10]2[CH:25]=[CH:26][C:27]([S:45][C:42]3[N:41]([CH3:46])[C:40]([C:37]4[CH:38]=[CH:39][C:34]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:35][CH:36]=4)=[N:44][N:43]=3)=[CH:28][C:9]=2[O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:14][CH:15]=1)[CH3:24]

참가 물질

6

반응물 3

HCID 28123BorohydrideHCID 86611168Ethyl [4-(2-heptyloxy-4-iodobenzylamino)phenyl]acetateHCID 178481686HCID 178481686, 화합물

생성물 1

HCID 11227433Ethyl(4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)acetate

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of ethyl [4-(2-heptyloxy-4-iodo benzylamino)phenyl]acetate obtained in Step d (4.11 g, 8.07 mmol) in a mixture of tetrahydrofuran (THF) (18 ml) and ethanol (18 ml) is added dropwise to a mixture of 5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazole-3-thiol (2.99 g, 12.1 mmol), bis(bipyridine)nickel (II) bromide (106 mg, 0.2 mmol) (Organometallics, 4, (1985), 657-661) and 9.68 g of borohydride polymer supported on Amberlite® IRA400 resin at 2.5 mmol/g (Aldrich) in 18 ml of a mixture of THF and ethanol 50:50. The mixture is heated for 20 hours under reflux, and then filtered at room temperature. The filtrate is concentrated using a rotary evaporator. The product is purified by chromatography on a silica column, eluted with a heptane/ethyl acetate 7:3 mixture. After evaporation of the solvents, 4.58 g (90%) of the expected compound are recovered in the form of an oil.

후처리

  1. temperatureThe mixture is heated for 20 hours
  2. temperatureunder reflux
  3. filtrationfiltered at room temperature
  4. concentrationThe filtrate is concentrated
  5. customa rotary evaporator
  6. customThe product is purified by chromatography on a silica column
  7. washeluted with a heptane/ethyl acetate 7:3 mixture
  8. customAfter evaporation of the solvents, 4.58 g (90%) of the expected compound
  9. customare recovered in the form of an oil

출처 및 근거

ORD 기록
ord-fe966cb0b4b5497d85742391141660b8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829588B2

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