Water → HCID 86618887, compound

HRID 252419Notes

Reaction equation

HRID 252419 reaction equation
[NH2:1][CH2:2][CH:3]([CH:5]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:6][CH:7]([CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[CH:16]=[C:15]2[CH2:22][CH2:23][CH2:24][O:25][CH3:26])[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][CH:3]([CH:5]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:6][CH:7]([CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[CH:16]=[C:15]2[CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH:8]([CH3:9])[CH3:10])[OH:4])=[O:46]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 62493Pivaloyl chlorideHCID 86618888HCID 86618888, compound

Product 1

HCID 86618887HCID 86618887, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The stirred solution of 0.035 g of tert-butyl {1-(2-amino-1-hydroxyethyl)-3-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-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 a further 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 identified on the basis of the Rf value from the residue.

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-934f63fd00d94e17b63bee39a767f4a4
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

Loading…