tert-Butanol → HCID 53403820, compound

HRID 1784032Notes

Reaction equation

HRID 1784032 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@H:7]1C(O)=O)=[O:5])C.CC[N:17]([CH2:20]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[CH3:39][C:40]([OH:43])([CH3:42])[CH3:41]>C1(C)C=CC=CC=1>[CH3:1][O:3][C:4]([CH:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][CH:7]1[NH:17][C:20]([O:43][C:40]([CH3:42])([CH3:41])[CH3:39])=[O:29])=[O:5]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 66882442HCID 66882442, compound

Product 1

HCID 53403820HCID 53403820, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2.03 g trans-(1SR,2SR)-4-methylene-cyclopentane-1,2-dicarboxylic acid ethyl ester (prepared and purified according to example 1 and 2, step 1) and 1.13 g of NEt3 in 25 ml of toluene was added drop wise at 22° C. 3.03 g of diphenylphosphoryl azide and the mixture was heated at 80° C. for 30 min. The mixture was diluted with 4.08 g of t-BuOH and heating was continued at 90° C. for 16 h. The mixture was evaporated and the residue chromatographed on silica using a gradient of CH2Cl2 to CH2Cl2/MeOH (99:1) to give 1.55 g (55%) of the title compound 35a.

Workup

  1. temperatureheating
  2. customThe mixture was evaporated
  3. customthe residue chromatographed on silica using a gradient of CH2Cl2 to CH2Cl2/MeOH (99:1)

Sources & evidence

ORD record
ord-948f02989d8747778707dea01672f602
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

Loading…