Ninhydrin → 6-Carboxyfluorescein succinimidyl ester

HRID 1468977Notes

Reaction equation

HRID 1468977 reaction equation
[CH:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]2[C:10]3([O:26][C:27](=[O:28])[C:3]=2[CH:2]=1)[C:20]1[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:19]=1[O:18][C:12]1[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]3=1.C1C=[C:33]2[C:35](C(O)(O)[C:38](=[O:39])[C:32]2=CC=1)=[O:36].CC[N:44](C(C)C)C(C)C.CN(C)C=O>>[CH2:32]1[C:38](=[O:39])[N:44]([O:8][C:7]([C:6]2[CH:1]=[CH:2][C:3]3[C:27]([O:26][C:10]4([C:20]5[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:19]=5[O:18][C:12]5[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]4=5)[C:4]=3[CH:5]=2)=[O:28])=[O:9])[C:35](=[O:36])[CH2:33]1

Participants

4

Reactant 3

HCID 10236NinhydrinHCID 768066-CarboxyfluoresceinHCID 21988380HCID 21988380, compound

Product 1

HCID 27626146-Carboxyfluorescein succinimidyl ester

Procedure

The resin was treated with 2 equivalents 6-FAM-NHS in 1% DIEA/N,N-dimethylformamide and stirred or shaken at ambient temperature overnight. When complete, the resin was drained, washed thrice with N,N-dimethylformamide, thrice with (1× DCM and 1× methanol) and dried to provide an orange resin that was negative by ninhydrin test.

Workup

  1. stirringshaken at ambient temperature overnight
  2. washwashed thrice with N,N-dimethylformamide, thrice with (1× DCM and 1× methanol)
  3. customdried
  4. customto provide an orange resin that

Sources & evidence

ORD record
ord-78f9527a84e0499fbe06c03f52470ae8
Source dataset
uspto-grants-2015_04
Patent number
US09006247B2

Reaction notes

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