Reaction equation
C1C=CC(OCCOC2C=CC=CC=2N(CC(O)=O)CC(O)=O)=C(N(CC(O)=O)CC(O)=O)C=1.[CH:35]1[C:40]([F:41])=[CH:39][C:38]([O:42][CH2:43][CH2:44][O:45][C:46]2[CH:51]=[C:50](F)[CH:49]=[CH:48][C:47]=2[N:53]([CH2:58][C:59]([OH:61])=[O:60])[CH2:54][C:55]([OH:57])=[O:56])=[C:37]([N:62]([CH2:67][C:68]([OH:70])=[O:69])[CH2:63][C:64]([OH:66])=[O:65])[CH:36]=1.[N+](C1C=CC([F:80])=C(F)C=1O)([O-])=O.CC1C=CC(N(CC(O)=O)CC(O)=O)=C(OCCOC2C=C3[CH:109]=[C:110]([C:112]4[O:116][C:115]([C:117]([OH:119])=[O:118])=[CH:114][N:113]=4)[O:111]C3=CC=2N(CC(O)=O)CC(O)=O)C=1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C>>[CH:36]1[C:37]([N:62]([CH2:67][C:68]([OH:70])=[O:69])[CH2:63][C:64]([OH:66])=[O:65])=[C:38]([O:42][CH2:43][CH2:44][O:45][C:46]2[CH:51]=[C:50]3[CH:109]=[C:110]([C:112]4[O:116][C:115]([C:117]([OH:119])=[O:118])=[CH:114][N:113]=4)[O:111][C:49]3=[CH:48][C:47]=2[N:53]([CH2:58][C:59]([OH:61])=[O:60])[CH2:54][C:55]([OH:57])=[O:56])[C:39]([F:80])=[C:40]([F:41])[CH:35]=1Participants
6
Procedure
As discussed above, the synthesis of 5,5', 6,6'-tetrafluoro-BAPTA (Formula II) was carried out as originally described for both BAPTA and 5,5'-difluoro BAPTA starting from commercially available 2-nitro-5,6-difluorophenol. Fura-F was synthesized via the pathway originally described for the preparation of Fura-2. Unless otherwise noted commercially available reagents and dry solvents were used as received. Reactions were carried out under an atmosphere of argon and reaction temperatures refer to the bath. Flash column chromatography was performed with Merck Silica Gel 60 (40-63 μm). Proton sponge is 1,8-bis(dimethylamino)naphthalene.
Workup
- customreaction temperatures
Sources & evidence
- ORD record
- ord-76d2846edae443ab9eed0f43a815ffed
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05516911
Linked notes
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