Ammonium Chloride → tert-Butyl (1(S)-(2-azido-1(S)-hydroxyethyl)-3(S)-{[2-(3-methoxypropoxy)benzoylamino]-methyl}4-methylpentyl)carbamate

HRID 507839Notes

Reaction equation

HRID 507839 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:33]=[CH:32][CH:31]=[CH:30][C:8]=1[C:9]([NH:11][CH2:12][C@H:13]([CH:27]([CH3:29])[CH3:28])[CH2:14][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C@@H:16]1[CH2:18][O:17]1)=[O:10].[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+]>CO>[N:34]([CH2:18][C@@H:16]([C@@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH2:14][C@H:13]([CH2:12][NH:11][C:9](=[O:10])[C:8]1[CH:30]=[CH:31][CH:32]=[CH:33][C:7]=1[O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:27]([CH3:29])[CH3:28])[OH:17])=[N+:35]=[N-:36]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86613450tert-butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)-(R)-oxiranylpentyl)-carbamate

Product 1

HCID 86613457tert-Butyl (1(S)-(2-azido-1(S)-hydroxyethyl)-3(S)-{[2-(3-methoxypropoxy)benzoylamino]-methyl}4-methylpentyl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 0.600 g of tert-butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)—(R)-oxiranylpentyl)carbamate (Example 1b) in 12 ml of methanol is admixed with 0.208 g of sodium azide and 0.123 g of ammonium chloride, and stirred at reflux over 6 hours. The reaction solution is cooled, poured onto ice-water and extracted with tert-butyl methyl ether (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=0.37 (2:1 EtOAc-heptane); Rt=18.95 (gradient II).

Workup

  1. temperatureat reflux over 6 hours
  2. temperatureThe reaction solution is cooled
  3. additionpoured onto ice-water
  4. extractionextracted with tert-butyl methyl ether (2×)
  5. washThe combined organic phases are washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b0666a9316da45f09d37424ea70ca055
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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