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

HRID 896279ノート

反応式

HRID 896279 の反応式
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]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 562880Methyl 2-(4-methylphenylsulfonamido)acetateHCID 5462977Diethyl azodicarboxylate2 回HCID 22346407Propan-2-yl 3-(hydroxymethyl)pyridine-2-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8fc8694ece2940d99494ad1188771846
出典データセット
uspto-grants-2005_07
特許番号
US06919351B2

反応ノート

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