Water → HCID 86613531, compound

HRID 2237732Notes

Reaction equation

HRID 2237732 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].N1C=CC=CC=1.[C:40](OC(=O)C)(=[O:42])[CH3:41].O>ClCCl>[C:40]([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:42])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 59588942HCID 59588942, compound

Product 1

HCID 86613531HCID 86613531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 0.040 g of tert-butyl {1(S)-(2-amino-1(S)-hydroxyethyl)-3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate in 2 ml of dichloromethane is admixed successively with 0.007 ml of pyridine and 0.011 ml of acetic anhydride and stirred at room temperature over 1 hour. The reaction solution is admixed with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with 1M HCl, 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=0.37 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=17.25 (gradient II).

Workup

  1. extractionextracted with tert-butyl methyl ether (2×)
  2. washThe combined organic phases are washed with 1M HCl, water and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-35e5681758ff424ab140801b5676a29d
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

Loading…