Water → HCID 86613456, compound

HRID 507838Notes

Reaction equation

HRID 507838 reaction equation
[NH2:1][CH2:2][C@@H:3]([C@@H:5]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:6][C@H:7]([CH2:11][NH:12][C:13](=[O:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH:8]([CH3:10])[CH3:9])[OH:4].C(=O)([O-])[O-].[Na+].[Na+].[C:41](Cl)(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43].O>C(OCC)(=O)C>[CH3:43][C:42]([CH3:45])([CH3:44])[C:41]([NH:1][CH2:2][C@@H:3]([C@@H:5]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:6][C@H:7]([CH2:11][NH:12][C:13](=[O:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH:8]([CH3:9])[CH3:10])[OH:4])=[O:46]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 62493Pivaloyl chlorideHCID 69176508HCID 69176508, compound

Product 1

HCID 86613456HCID 86613456, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The stirred solution of 0.030 g of tert-butyl (1(S)-(2-amino-1(S)-hydroxyethyl)-3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}4-methylpentyl)carbamate in 0.60 ml of ethyl acetate is admixed successively with 0.60 ml of 2M sodium carbonate solution and 0.012 ml of pivaloyl chloride and stirred at room temperature over 1 hour. The reaction solution is admixed with water and extracted with ethyl acetate (2×). The combined organic phases are washed 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=0.45 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=4.71 (gradient I)

Workup

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

Sources & evidence

ORD record
ord-d48e25508bf54f73b77035e1b2574968
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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