Triphenylphosphine → Tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate

HRID 595114ノート

反応式

HRID 595114 の反応式
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Br:15][C:16]1[C:17]([OH:41])=[C:18]([C:23]([N:26]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:24][CH:25]=1)[C:19]([O:21][CH3:22])=[O:20].O[CH2:43][CH:44]1[CH:48]=[CH:47][CH2:46][N:45]1[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:15][C:16]1[C:17]([O:41][CH2:43][CH:44]2[CH:48]=[CH:47][CH2:46][N:45]2[C:49]([O:51][C:52]([CH3:53])([CH3:55])[CH3:54])=[O:50])=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:23]([N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:24][CH:25]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11095619tert-butyl 2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylateHCID 70983234Methyl 3-bromo-6-bis-(tert-butoxycarbonyl)amino-2-hydroxybenzoate2 回

生成物 1

HCID 86712822Tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate収率 113.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diisopropylazodicarboxylate (1.4 g) was added to a suspension of methyl 3-bromo-6-[bis-(tert-butoxycarbonyl)amino]-2-hydroxybenzoate (Intermediate 13, 2.58 g), tert-butyl 2-hydroxymethyl-2,5-dihydropyrrole-1-carboxylate (Prepared according to Morriello et al, Bioorg. Med. Chem, 2008, 16(5), 2156; 1.27 g) and triphenylphosphine (1.82 g) in anhydrous THF (20 mL) and the mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-25% to give tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate (4.13 g) as a light brown oil.

後処理

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-25%

出典と根拠

ORDレコード
ord-1da8d55a5bd4431180ca2f5d19eb67c3
出典データセット
uspto-grants-2016_01
特許番号
US09242997B2

反応ノート

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