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

HRID 2249620
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HRID 2249620 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매2회
HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-cad6fd82053144fc86f196539b7bfb7b
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07314888B1

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