Acetic Acid → HCID 178444181, compound

HRID 582177Notes

Reaction equation

HRID 582177 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][OH:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[PH:11](=[O:14])([OH:13])[OH:12].[CH2:15]([C:17]([CH2:45][CH3:46])([CH:19](Br)[C:20]1[N:24]=[CH:23][N:22]([C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:21]=1)[CH3:18])[CH3:16].C(O)(=O)C>C(O)C>[PH:11](=[O:12])([OH:14])[OH:13].[CH2:45]([C:17]([CH2:15][CH3:16])([CH:19]([O:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])[C:20]1[N:24]=[CH:23][N:22]([C:25]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:21]=1)[CH3:18])[CH3:46]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 961HydroxideHCID 97534tert-butyl N-hydroxycarbamateHCID 178442503HCID 178442503, compound

Product 1

HCID 178444181HCID 178444181, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of t-butyl-N-hydroxycarbamate (0.25 g) in ethanol (10 ml) was treated with postassium hydroxide (0.10 g), then diethyl 3-bromo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 29) added. The mixture was allowed to stand for twenty hours, poured into ice-water, neutralized with a little acetic acid and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulphate, and evaporated under reduced pressure to give crude diethyl 3-t-butoxycarbonylaminoxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.14 g) as a colourless gum. NMR (CDCl3): δ 1.3(6H,t), 1.4(9H,s), 1.5-1.8(2H,m), 2.2-2.3(2H,m), 4.1(4H,m), 5.0(1H,t), 7.1(6H,m), 7.3(9H,m), 7.95(1H,s). M/S: M+ 620.

Workup

  1. waitto stand for twenty hours
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-77eaf3e878ec454080346e48c6fe416c
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

Loading…