Ethyl Acetate → HCID 86613536, compound

HRID 2237738Notes

Reaction equation

HRID 2237738 reaction equation
[NH2:1][CH2:2][C@@H:3]([C@@H:5]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:6][C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH:13]=1)[CH:8]([CH3:10])[CH3:9])[OH:4].C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[C:46](Cl)(=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48]>O>[CH3:48][C:47]([CH3:50])([CH3:49])[C:46]([NH:1][CH2:2][C@@H:3]([C@@H:5]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:6][C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH:13]=1)[CH:8]([CH3:10])[CH3:9])[OH:4])=[O:51]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 62493Pivaloyl chlorideHCID 59588942HCID 59588942, compound

Product 1

HCID 86613536HCID 86613536, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The stirred solution of 0.025 g of tert-butyl {1(S)-(2-amino-1(S)-hydroxyethyl)-3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate (Example 36b) and 0.230 ml of ethyl acetate is admixed at 0° C. successively with 0.230 ml of 2M sodium carbonate solution and 0.007 ml of pivaloyl chloride, and stirred at room temperature over another 4 hours. The reaction solution is admixed with water and extracted with ethyl acetate (2×). The combined organic phases are washed successively with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a colourless oil. Rf=0.61 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=5.05 (gradient I).

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organic phases are washed successively with water and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fe5e4baffc3944e79376db63638c649c
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

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