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Hydrochloric Acid → benzyl 2-(2-isobutoxy-5-{[(2R,4R)-4-isobutoxy-2-(4-methylpentyl)pyrrolidinyl]carbonyl}phenyl)acetate

HRID 2249620
ノート
印刷プレビュー

反応式

HRID 2249620 の反応式
[CH2:1]([O:5][C@H:6]1[CH2:10][NH:9][C@H:8]([CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:7]1)[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.[CH2:24]([O:31][C:32]([CH2:34][C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][C:43]=1[O:44][CH2:45][CH:46]([CH3:48])[CH3:47])[C:38](Cl)=[O:39])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>O1CCCC1.O.C(OCC)(=O)C>[CH2:45]([O:44][C:43]1[CH:42]=[CH:41][C:37]([C:38]([N:9]2[CH2:10][C@H:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:7][C@H:8]2[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[O:39])=[CH:36][C:35]=1[CH2:34][C:32]([O:31][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:33])[CH:46]([CH3:48])[CH3:47]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 178164493-(Benzyloxycarbonylmethyl)-4-isobutoxybenzoyl chlorideHCID 68984938(2R,4R)-4-isobutoxy-2-(4-methylpentyl)pyrrolidine

生成物 1

HCID 68986435benzyl 2-(2-isobutoxy-5-{[(2R,4R)-4-isobutoxy-2-(4-methylpentyl)pyrrolidinyl]carbonyl}phenyl)acetate

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒2 回
HCID 8857Ethyl Acetate溶媒

実験手順

In 4.8 ml of tetrahydrofuran are dissolved 0.16 g of (2R,4R)-4-isobutoxy-2-(4-methylpentyl)pyrrolidine and 0.78 ml of triethylamine, to which is dropwise added a solution of 3-(benzyloxycarbonylmethyl)-4-isobutoxybenzoyl chloride in tetrahydrofuran (prepared from 0.48 g of 3-(benzyloxycarbonylmethyl)-4-isobutoxybenzoic acid, 0.09 ml of oxalyl chloride and 4.8 ml of tetrahydrofuran) at 5-10° C. The mixture thus obtained is stirred at ambient temperature for 15 hours. Ethyl acetate and water are added to the reaction mixture, pH is adjusted to 3.0 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography [eluent; n-hexane:ethyl acetate=3:1] to obtain 0.18 g of benzyl 2-(2-isobutoxy-5-{[(2R,4R)-4-isobutoxy-2-(4-methylpentyl)pyrrolidinyl]carbonyl}phenyl)acetate as a yellow-colored oily product.

後処理

  1. customThe mixture thus obtained
  2. customthe organic layer is separated
  3. customThe organic layer thus obtained
  4. washis washed with water and saturated aqueous solution of sodium chloride successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe residue thus obtained
  8. customis purified by silica gel column chromatography [eluent; n-hexane:ethyl acetate=3:1]

出典と根拠

ORDレコード
ord-cad6fd82053144fc86f196539b7bfb7b
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07314888B1

反応ノート

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