Thionyl Chloride → HCID 53970757, compound

HRID 843293Notes

Reaction equation

HRID 843293 reaction equation
[CH:1]1C2C(COC(N[C@H](CO)CCC)=O)C3C(=CC=CC=3)C=2C=CC=1.[C:25]([NH:42][C@H:43]([C:47]([OH:49])=[O:48])[CH2:44][CH2:45][CH3:46])([O:27][CH2:28][CH:29]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26].S(Cl)(Cl)=O>CO.C(OCC)(=O)C>[CH3:1][O:48][C:47](=[O:49])[C@H:43]([CH2:44][CH2:45][CH3:46])[NH:42][C:25]([O:27][CH2:28][CH:29]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=2[C:36]2[C:41]1=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:26]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 7016885Fmoc-L-norvalineHCID 21015970HCID 21015970, compound

Product 1

HCID 53970757HCID 53970757, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

FIG. 11 depicts a reaction scheme for the synthesis of 11-2b, 9-fluorenylmethoxy-carbonyl-norvalinol, a description of the synthesis of which follows. To a chilled solution of 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. Thin layer chromatography in ethyl acetate after an hour confirmed the completion of the reaction (Rf=0.85). The reaction mixture was concentrated and the remaining residue was dissolved in ethyl acetate. The organic layer was washed with several 200 ml portions of saturated sodium bicarbonate followed by brine. The organic layer was dried and concentrated to afford the title compound 9-fluorenylmethoxy-carbonyl-norvaline methyl ester 11-2a 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. customa reaction scheme
  2. customa description of the synthesis of which
  3. customthe completion of the reaction (Rf=0.85)
  4. concentrationThe reaction mixture was concentrated
  5. dissolutionthe remaining residue was dissolved in ethyl acetate
  6. washThe organic layer was washed with several 200 ml portions of saturated sodium bicarbonate
  7. customThe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-21dcbc03a06b437ba2ae5a4e9795a041
Source dataset
uspto-grants-2002_04
Patent number
US06376649B1

Reaction notes

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