Dimethyl Sulfoxide → HCID 10596254, 화합물

HRID 2121271노트

반응식

HRID 2121271 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13](=[O:37])[C@H:14]([CH2:33][CH2:34][S:35][CH3:36])[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][C:18]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31].C(N(CC)CC)C>C(Cl)Cl.CCOCC>[CH3:11][O:12][C:13](=[O:37])[C@H:14]([CH2:33][CH2:34][S:35][CH3:36])[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][C:18]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 54396972N-[4-Hydroxymethyl-2-(2-methylphenyl)benzoyl]methionine methyl ester

생성물 1

HCID 10596254HCID 10596254, 화합물수율 60.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

To a mechanically stirred solution at −78° C. under N2 of anhydrous DMSO (16.9 mL, 1.08 mol) in CH2Cl2 (750 mL) was added dropwise via addition funnel oxalyl chloride (44.8 mL, 513 mmol) such that temperature was maintained below −65° C. The reaction was stirred 15 minutes, and a solution of N-[4-Hydroxymethyl-2-(2-methylphenyl)benzoyl]methionine methyl ester (110 g, 285 mmol), prepared as in example 1075F, in CH2Cl2 (100 mL) was added dropwise via addition funnel such that temperature was again maintained below −65° C. After one hour, triethylamine (159 mL, 1.14 mol) was added, and the reaction was warmed to ambient temperature over one hour. The reaction was poured into ether (1.5 L) and washed with brine (2×1.5 L). The organic layer was dried with Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (30% EtOAC/Hexanes) to give the desired product as a pale yellow solid (66 g, 60%). 1H(300 MHz, CDCl3) δ 11.00 (1H, s), 8.07 (1H, m), 7.97 (1H, dd, J=8, 2 Hz), 7.75 (1H, bs), 7.40-7.20 (4H, bs), 6.01 (1H, m), 4.63 (1H, m), 3.68 (3H, s), 2.20-2.00 (8H, m), 1.87 (1H, m), 1.63 (1H, m). m/e (ESI) 384 (MH−).

후처리

  1. temperaturewas maintained below −65° C
  2. customwas again maintained below −65° C
  3. waitAfter one hour
  4. washwashed with brine (2×1.5 L)
  5. dry with materialThe organic layer was dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (30% EtOAC/Hexanes)

출처 및 근거

ORD 기록
ord-15e4b3e2708844169f7a64041d9c6b87
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693123B2

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