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

HRID 2394479ノート

反応式

HRID 2394479 の反応式
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

参加物

4

反応物 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

生成物 1

HCID 11345724N-Benzoyl-L-glutamic acid

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7c2f8a92ff934aa9a22ebde881a01881
出典データセット
uspto-grants-1998_09
特許番号
US05811454

反応ノート

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