Triphenylphosphine → HCID 59403498, compound

HRID 1514217Notes

Reaction equation

HRID 1514217 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].O[C:27]1[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:28]=1[C:29]([O:31][CH3:32])=[O:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:23][C:21]([O:20][C:19]([NH:18][CH2:17][CH2:16][O:15][C:27]1[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:28]=1[C:29]([O:31][CH3:32])=[O:30])=[O:25])([CH3:22])[CH3:24]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 80651Methyl 3-methoxysalicylateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 59403498HCID 59403498, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (23.95 ml, 123 mmol) was added dropwise to a stirred solution of 1,1-dimethylethyl (2-hydroxyethyl)carbamate (18.05 g, 112 mmol), methyl 2-hydroxy-3-(methyloxy)benzoate (20.4 g, 112 mmol) and triphenylphosphine (32.3 g, 123 mmol) in THF (400 ml) with cooling in an ice/water bath. Stirred for 30 mins then evaporated and used without any purification. LC/MS showed essentially just product and triphenylphosphine oxide. Yield 98.9 g of crude material. MS (ES): C16H23NO6 requires 325; found 326 [M+H]+.

Workup

  1. temperaturewith cooling in an ice/water bath
  2. customthen evaporated
  3. customused without any purification

Sources & evidence

ORD record
ord-e99ff6ed66af4405ad81e8843252738e
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

Loading…