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

HRID 2249620Notes

Reaction equation

HRID 2249620 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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]

Sources & evidence

ORD record
ord-cad6fd82053144fc86f196539b7bfb7b
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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