Di-tert-butyl 3-fluoro,4-[Bis(2-(mesyloxy)ethyl)amino]benzoyl-L-glutamate → N-Benzoyl-L-glutamic acid

HRID 2394479Notes

Reaction equation

HRID 2394479 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)[C:5]([NH:7][C@H:8]([C:18]([O:20]C(C)(C)C)=[O:19])[CH2:9][CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])=[O:6].FC1C=C(C=CC=1N(CCCl)CCCl)C(N[C@H](C(OC(C)(C)C)=O)CCC(OC(C)(C)C)=O)=O>C(O)(C(F)(F)F)=O>[C:5]([NH:7][C@H:8]([C:18]([OH:20])=[O:19])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:6])[C:4]1[CH:3]=[CH:2][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 10439134Di-tert-butyl 3-fluoro,4-[Bis(2-(mesyloxy)ethyl)amino]benzoyl-L-glutamateHCID 11756461Di-tert-butyl 3-fluoro,4-[Bis(2-chloroethyl)amino]benzoyl-L-glutamate

Product 1

HCID 11345724N-Benzoyl-L-glutamic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound (16) (0.10 g, 0.16 mmol), (17) (0.08 g, 0.13 mmol), or (18) (0.06 g, 0.11 mmol) was suspended in TFA (4% w/v) and stirred for 40 min at room temperature. The acid was removed under reduced pressure and the remaining oil was diluted with ethyl acetate (1 ml) which was evaporated. This latter step was repeated 5-6 times. Compound (19); yield (0.09 g, 91%) 3-fluoro, 4-[bis-[2-mesyloxy)ethyl]amino]benzoyl-L-glutamic acid, was obtained as a pure product from (16); 1H NMR (Me2 SO-d6)δ1.99 (m, 2H, CH2CH2CO2H), 2.35 (t, 2H, J=7.45 Hz, CH2CH2CO2H), 3.13 (s, 6H, (CH3 SO3)2), 3.72 (t, 4H,J=5.34 Hz, (CH3SO3CH2 CH2)2), 4.31 (t, 4H, J=5.16 Hz, (CH3SO3CH2 CH2)2), 4.39 (m, 1H, CH), 7.16 (dd, 1H, JH-5,H-6 =8.59, JH-5,F =18.03 Hz, H-5), 7.68 (dd, JH-6,H-5 =8.91, JH-2,F =15.29 Hz, H-2, H-6), 8.45 (d, 1H, J=7.69 Hz, NH); 19F NMR (Me2SO-d6) δ-122.54(m); mass spectrum (FAB) m/z (529[M+H+ ],45) 382 (M-glu, 100); Accurate mass expected 529.0961 found +5.4 ppm; Anal: C18H25N2O11FS2 -0.22TFA-0.21EtOAc requires C-40.47, H-4.74, N-4.90, F-5.51, S-11.21, found C-40.87, H-4.76, N-4.75, F-5.85, S-10.98. (The presence of EtOAc and TFA, noted in the elemental analysis was confirmed by NMR). This compound reacted positively with the Epstein spray reagent.

Workup

  1. customThe acid was removed under reduced pressure
  2. additionthe remaining oil was diluted with ethyl acetate (1 ml) which
  3. customwas evaporated

Sources & evidence

ORD record
ord-7c2f8a92ff934aa9a22ebde881a01881
Source dataset
uspto-grants-1998_09
Patent number
US05811454

Reaction notes

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