Benzyl chloroformate → 3-[3-(Naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1711394ノート

反応式

HRID 1711394 の反応式
C([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([CH2:23][S:24]([C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:15]=2)[CH2:9]1)C1C=CC=CC=1.[CH2:37]([O:44][C:45](Cl)=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[OH-].[Na+]>C1C=CC=CC=1>[CH2:37]([O:44][C:45]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([CH2:23][S:24]([C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:15]=2)[CH2:9]1)=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 588286161-Benzyl-3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine

生成物 1

HCID 588286253-[3-(Naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine-1-carboxylic acid benzyl ester収率 70%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A solution of 1-benzyl-3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine (4.2 g, 8.4 mmol) and benzylchloroformate (12.0 mL, 84 mmol in 2 equal portions) in benzene was heated at reflux temperature, under nitrogen, for 3 hours, cooled to ambient temperatures, poured into 2.5 N sodium hydroxide and extracted with ethyl acetate. The extracts were combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography using 40-50% ethyl acetate in hexane to afford 3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine-1-carboxylic acid benzyl ester as a buff foam, 3.2 g (70% yield), Mass spectrum (+EI, [M+H]+) m/z 547. 1HNMR (500 MHz, DMSO-d6): δ8.46 (d, 1H, J=7.44 Hz), 8.27 (d, 1H, J=8.06 Hz), 8.06-8.08 (m, 1H), 7.94-7.99 (m, 2H), 7.57-7.68 (m, 3H), 7.26-7.39 (m, 5H), 7.09 (dd, 1H, J=9.15 Hz and 2.68 Hz), 6.77 (s, 1H), 5.19-5.26 (m, 2H), 5.01-5.10 (m, 2H), 4.90 (s, 1H), 3.42-3.59 (m, 2H), 3.31-3.36 (m, 1H), 1.98-2.10 (m, 1H), 1.79-1.86 ppm (m, 1H).

後処理

  1. temperatureat reflux temperature
  2. temperaturecooled to ambient temperatures
  3. extractionextracted with ethyl acetate
  4. washwashed sequentially with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-ff7824d770f14d898ac6455f897fda26
出典データセット
uspto-grants-2010_09
特許番号
US07790751B2

反応ノート

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