Sodium Carbonate → HCID 131728265, compound

HRID 499703Notes

Reaction equation

HRID 499703 reaction equation
[CH3:1][O:2][C:3](=[O:35])[NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:15](=[O:34])[CH2:16][C:17]([CH3:33])([CH3:32])[CH2:18][C@H:19]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@@H:20]([OH:23])[CH2:21][NH2:22])[CH2:6]1.C(=O)([O-])[O-].[Na+].[Na+].[C:42](Cl)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:35])[NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:15](=[O:34])[CH2:16][C:17]([CH3:33])([CH3:32])[CH2:18][C@H:19]([NH:24][C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[C@@H:20]([OH:23])[CH2:21][NH:22][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 62493Pivaloyl chlorideHCID 69176521HCID 69176521, compound

Product 1

HCID 131728265HCID 131728265, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.030 g of [1-(7-amino-5(S)-tert-butoxycarbonylamino-6(S)-hydroxy-3,3-dimethyl-heptanoyl)-1,2,3,4-tetrahydro-quinolin-3(R,S)-yl]-carbamic acid methyl ester in 0.6 ml of ethyl acetate at room temperature under argon is added 0.6 ml of saturated aqueous sodium carbonate solution. The mixture is stirred for 15 minutes at room temperature and and 0.011 ml of pivaloyl chloride are added. The mixture is stirred at room temperature for 1.5 hours. The layers are separated and the aqueous layer is extracted with ethyl acetate (2×). The combined organic layers are dried over sodium sulphate, filtered and concentrated. The title compound is obtained as a beige oil from the residue by means of flash chromatography (SiO2 60 F). Rt=4.46 (gradient I).

Workup

  1. stirringThe mixture is stirred at room temperature for 1.5 hours
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic layers are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-345547ac3e9d48899f9ab2cb3eeebd29
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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