Triphenylphosphine → 3-{[Methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-pyridine-2-carboxylic Acid Isopropyl Ester

HRID 1760160노트

반응식

HRID 1760160 반응식
O[CH2:2][C:3]1[C:4]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])(=[O:24])=[O:23])=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:12]([O:11][C:9]([C:4]1[C:3]([CH2:2][N:25]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[S:22]([C:19]2[CH:18]=[CH:17][C:16]([CH3:15])=[CH:21][CH:20]=2)(=[O:24])=[O:23])=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:10])([CH3:14])[CH3:13]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 562880Methyl 2-(4-methylphenylsulfonamido)acetateHCID 5462977Diethyl azodicarboxylate2회HCID 22346407Propan-2-yl 3-(hydroxymethyl)pyridine-2-carboxylate

생성물 1

HCID 599831603-{[Methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-pyridine-2-carboxylic Acid Isopropyl Ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Isopropyl 3-(hydroxymethyl)pyridine-2-carboxylate (prepared in accordance with P. Ornstein et. al. J. Med. Chem. 1989, 32, 827) (200 g, 1.02 mol), methyl N-[(4-methylphenyl)sulfonyl]glycinate (249 g, 1.02 mol), and triphenylphosphine (403 g, 1.5 mol) were dissolved in dry THF (3000 mls) and cooled to zero degrees under N2. The diethylazodicarboxylate (DEAD) (267.6 g, 1.5 mol) was dissolved in dry THF (250 mls) and placed in a 500 ml addition funnel. The DEAD was added dropwise over 1 hour. The ice bath was removed and the reaction was allowed to warm slowly to RT. After 2 hours, the reaction was checked by HPLC (above conditions) and some glycinate remained. More starting reagents were added and the reaction was left to stir at RT. After 30 min, the reaction was checked again and saw a very small amount of the glycinate remaining. Concentrated reaction down to a reddish-orange oil that was carried onto the next step.

후처리

  1. temperaturecooled to zero degrees under N2
  2. additionplaced in a 500 ml addition funnel
  3. customThe ice bath was removed
  4. additionwere added
  5. waitthe reaction was left
  6. waitAfter 30 min
  7. concentrationConcentrated
  8. customreaction down to a reddish-orange oil that

출처 및 근거

ORD 기록
ord-d75fb16893d04578abbf3eb6b2a7cfdf
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06841558B2

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