Tris(hydroxymethyl)aminomethane → HCID 131716350, compound

HRID 1073491Notes

Reaction equation

HRID 1073491 reaction equation
C1C(=O)N([O:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[C:13](C3C4C=CC(O)=CC=4OC4C=3C=CC(C=4)=O)[CH:12]=2)=[O:10])C(=O)C1.C1C(=O)N(OC(C2C([C:52]3[C:62]4[CH:63]=[CH:64][C:65]([OH:67])=[CH:66][C:61]=4[O:60][C:59]4[C:53]=3[CH:54]=[CH:55][C:56]([CH:58]=4)=[O:57])=C(C(O)=O)C=CC=2)=O)C(=O)C1.[CH2:71]([OH:78])[C:72]([NH2:77])([CH2:75][OH:76])[CH2:73][OH:74].C(N(CC)CC)C>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH:15]1[C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:12]2[C:52]3([O:10][C:9](=[O:8])[C:11]=2[CH:16]=1)[C:53]1[CH:54]=[CH:55][C:56]([OH:57])=[CH:58][C:59]=1[O:60][C:63]1[CH:64]=[C:65]([OH:67])[CH:66]=[CH:61][C:62]3=1.[CH2:71]([C:72]([NH-:77])([CH2:75][OH:76])[CH2:73][OH:74])[OH:78]

Participants

6

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 162115733-{[(2,5-Dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid--4-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid (1/1)

Product 1

HCID 131716350HCID 131716350, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A 1000 ml round bottom flask was charged with 63.4 g (0.134 mole) of 5(6)-carboxyfluorescein N-hydroxysuccinimide ester, and 16.2 g (0.134 mole), of tris(hydroxymethyl)aminomethane, and 33.8 g (0.335 mole) of triethylamine. The contents of the flask were dissolved in 200 ml of dry dimethylformamide and stirred under nitrogen for 24 hours. A trace of 4-dimethylaminopyridine was added and the reaction was heated under nitrogen for another hour at 70° C. At the end of this period the reaction appeared complete by thin layer chromatography. The solvent was reduced down to a total volume of 200 ml of a dark red oily solution. This material was purified on preparatory HPLC apparatus using silica gel column and an elution solvent of acetic acid:2-propanol:ethyl acetate (2 8:70). The yield obtained was 20.5 g (32%). The desired structure was confirmed by 1H-NMR (CD3OD) which gave the following chemical shifts:

Workup

  1. customThis material was purified on preparatory HPLC apparatus
  2. customThe yield obtained
  3. customgave the following chemical shifts

Sources & evidence

ORD record
ord-a25c7073a31744f1a085bca1809160e2
Source dataset
uspto-grants-1990_11
Patent number
US04970074

Reaction notes

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