Methanol → HCID 53970757, compound

HRID 1743750Notes

Reaction equation

HRID 1743750 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-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 several 200 ml portions of saturated sodium bicarbonate followed by brine. The organic layer was dried, filtered and concentrated to afford Fmoc-norVal-OMe) 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. dissolutionthe remaining residue was dissolved in ethylacetate
  4. washThe organic layer was washed with several 200 ml portions of saturated sodium bicarbonate
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-04334b6ded6e49559a9b5faabefde499
Source dataset
uspto-grants-2006_03
Patent number
US07012066B2

Reaction notes

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