Thionyl Chloride → HCID 18728951, compound

HRID 392015Notes

Reaction equation

HRID 392015 reaction equation
[C:1]([NH:18][C@H:19]([C:23](O)=[O: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].S(Cl)(Cl)=O>CO.C(OC(=O)C)C>[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

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 7016885Fmoc-L-norvaline

Product 1

HCID 18728951HCID 18728951, compoundYield 109.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a chilled solution of Fmoc-norvaline (25 g, 73.75 mmol) in anhydrous methanol (469 mL) was added thionyl chloride (53.76 mL, 0.74 mol) over one hour. Thin layer chromatography in ethylacetate taken an hour later confirmed the completion of the reaction (Rf=0.85). The reaction mixture was concentrated and the remaining residue was picked-up in ethylacetate. The organic layer was washed with three 200 ml portions of saturated sodium bicarbonate followed by brine. The organic layer was dried and concentrated to afford the title product as a white solid (26.03 g) in quantitative yield. NMR δ ppm (CD3OD): 7.7 (m, 2H), 7.6 (m, 2H), 7.4 (m, 2H), 7.3 (m, 2H), 4.3 (m, 2H), 4.1 (m, 2H), 3.7 (s, 3H), 1.7 (m, 1H), 1.6 (m,1H), 1.4 (m, 2H), 0.95 (t, 3H).

Workup

  1. customthe completion of the reaction (Rf=0.85)
  2. concentrationThe reaction mixture was concentrated
  3. washThe organic layer was washed with three 200 ml portions of saturated sodium bicarbonate
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f551a40af624ac0b199d0b2474eb5ba
Source dataset
uspto-grants-2004_10
Patent number
US06800434B2

Reaction notes

Loading…