Sodium Carbonate → Boc-4-(3-pyridyl)phenylalanine methyl ester

HRID 1530935노트

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HRID 1530935 반응식
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)([O-])[O-].[Na+].[Na+].C(B(CC)[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)C>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 10319078N-Boc-4-iodophenylalanine methylester

생성물 1

HCID 15379602Boc-4-(3-pyridyl)phenylalanine methyl ester수율 47%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of N-Boc-4-iodo-L-phenylalanine methyl ester (810 mg, 2 mmol, Lei, H et al, ibid) tetrakis(triphenylphosphine)palladium (0) (231 mg, 0.2 mmol), aqueous sodium carbonate (4 mmol, 2 ml of a 2M solution) and diethyl(3-pyridyl)borane (294 mg, 2 mmol) in dimethoxyethane (30 ml) was refluxed for 6 hr. The solvent was removed in vacuo, the residue dissolved in EtOAc (100 ml) and washed with water (30 ml) aqueous sodium thiosulphate (20 ml) and brine (30 ml) dried (Na2SO4)and evaporated in vacuo. Purification by column chromatography (SiO2, EtOAc/hexane 30:70) gave the title compound (335 mg,47%) as a yellow oil. δH (CDCl3) 8.81 (1 H, d, J 1.7 Hz, PyrH), 8.56 (1 H, dd, J 4.8, 1.6 Hz, PyrH), 7.84 (1 H, dt, J 7.9, 2.0 Hz, PyrH), 7.49 (2 H, d, J 8.2 Hz, ArH), 7.34 (1 H, ddd, J 7.9, 4.8, 0.6 Hz, PyrH), 7.23 (2 H, d, J 8.2 Hz, ArH), 5.09 (1 H, br d, J 7.8 Hz, CONH), 4.62 (1 H, br q, J 6.8 Hz, CHα), 3.73 (3 H, s, CO2Me), 3.18 (1 H, dd, J 13.8, 5.6 Hz, CHAHBAr), 3.07 (1 H, dd, J 13.8, 5.8 Hz, CHAHBAr) and 1.40 (9 H, s, tBu); m/z (ESI, 15 V) 357 (MH+).

후처리

  1. temperaturewas refluxed for 6 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc (100 ml)
  4. washwashed with water (30 ml) aqueous sodium thiosulphate (20 ml) and brine (30 ml) dried (Na2SO4)and
  5. customevaporated in vacuo
  6. customPurification by column chromatography (SiO2, EtOAc/hexane 30:70)

출처 및 근거

ORD 기록
ord-74e0886f6f5149fa8dc319aded37deff
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06197794B1

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