Hydrochloric Acid → (E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid

HRID 12590Notes

Reaction equation

HRID 12590 reaction equation
C([O:3][C:4](=[O:33])/[CH:5]=[CH:6]/[C@@:7]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH3:24])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=1)C.[OH-].[Li+].CCOC(C)=O.Cl>CO.C1COCC1.O>[C:29]([O:28][C:26]([NH:25][C@:7]([CH3:24])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=1)/[CH:6]=[CH:5]/[C:4]([OH:33])=[O:3])=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 58897683(E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid ethyl ester

Product 1

HCID 58897682(E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (E)-(R)-4-tert-butoxycarbonylamino-6-(4-heptyloxy-phenyl)-4-methyl-hex-2-enoic acid ethyl ester (56 mg, 0.12 mMol) in methanol (0.5 ml), THF (0.5 ml) and water (0.5 ml) is added lithium hydroxide (14 mg, 0.61 mMol). The mixture is stirred at RT for 3.5 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and HCl (aqueous, 1 M). The aqueous phase is extracted twice with AcOEt. The combined organic layers are washed with a small amount of NaHCO3 (saturated aqueous solution), dried (Na2SO4) and concentrated under reduced pressure to give the title compound. The crude product is sufficiently pure to be used in the next stage without further purification.

Workup

  1. extractionThe aqueous phase is extracted twice with AcOEt
  2. washThe combined organic layers are washed with a small amount of NaHCO3 (saturated aqueous solution)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91458b10ebb940e4819c2a5ed4ed83e3
Source dataset
uspto-grants-2010_06
Patent number
US07728020B2

Reaction notes

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