Methanol → HCID 53970757, compound

HRID 1375340Notes

Reaction equation

HRID 1375340 reaction equation
[C:1]([NH:18][C@H:19]([C:23]([OH:25])=[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.[CH3:30]O>C(OC(=O)C)C>[NH:18]([C:1]([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2])[C@H:19]([C:23]([O:25][CH3:30])=[O:24])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7016885Fmoc-L-norvaline

Product 1

HCID 53970757HCID 53970757, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a chilled solution of the commercially available Fmoc-L-norvaline (25 g, 73.75 mmol) in anhydrous methanol (469 ml) was added thionyl chloride (53.76 ml, 737.5 mmol) over one hour. TLC 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 dissolved in ethylacetate. The organic layer was washed with saturated sodium bicarbonate (3×200 ml) followed by brine (200 ml). The organic layer was dried, filtered and concentrated to afford Fmoc-norVal-OMe as a white solid (26.03 g) in quantitative yield. NMR * 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. dissolutionthe remaining residue was dissolved in ethylacetate
  4. washThe organic layer was washed with saturated sodium bicarbonate (3×200 ml)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-60eb2fe638e0466d8cb9d32fb8a2fa13
Source dataset
uspto-grants-2007_01
Patent number
US07169760B2

Reaction notes

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