Triethylamine → HCID 18728951, compound

HRID 734206Notes

Reaction equation

HRID 734206 reaction equation
[C:1]([NH:18][C@H:19]([CH2:23][OH:24])[CH2:20][CH2:21][CH3:22])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].C(N(CC)CC)C.C(OC(=O)C)C>ClCCl.CS(C)=O>[CH:7]1[C:6]2[CH:5]([CH2:4][O:3][C:1]([NH:18][C@H:19]([CH:23]=[O:24])[CH2:20][CH2:21][CH3:22])=[O:2])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21015970HCID 21015970, compound

Product 1

HCID 18728951HCID 18728951, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Fmoc-norValinol (21.70 g, 66.77 mmol) in dichloromethane (668 ml) was added triethylamine (37.23 ml, 267 mmol) and the solution was cooled to 0° C. A suspension of pyridine sulfur trioxide complex (42.51 g, 267 mmol) in dimethylsulfoxide (96 ml) was added to the chilled solution. After one hour, TLC in 2:3 ethylacetate:hexanes confirmed the completion of the reaction. The dichloromethane was removed under reduced pressure and the remaining residue was dissolved in ethylacetate and washed with water (2×50 ml), 1 N saturated sodium bisulfate (2×50 ml), saturated sodium bicarbonate (2×50 ml) and brine (50 ml). The organic layer was concentrated to yield a white solid. Theoretical yield (21.57 g) was assumed and the reaction was taken to the next step without further purification.

Workup

  1. additionwas added to the chilled solution
  2. customthe completion of the reaction
  3. customThe dichloromethane was removed under reduced pressure
  4. dissolutionthe remaining residue was dissolved in ethylacetate
  5. washwashed with water (2×50 ml), 1 N saturated sodium bisulfate (2×50 ml), saturated sodium bicarbonate (2×50 ml) and brine (50 ml)
  6. concentrationThe organic layer was concentrated
  7. customto yield a white solid
  8. customTheoretical yield (21.57 g)
  9. customthe reaction was taken to the next step without further purification

Sources & evidence

ORD record
ord-b7dbece5f18d414188266466cbd627a6
Source dataset
uspto-grants-2009_09
Patent number
US07592316B2

Reaction notes

Loading…