Tris(hydroxymethyl)aminomethane → HCID 67304415, compound

HRID 1009891Notes

Reaction equation

HRID 1009891 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][CH2:14][CH2:15][C:16]1[CH:56]=[CH:55][C:19]([CH2:20][C:21]2[C:22]([CH3:54])=[CH:23][C:24]([O:50][C:51](=[O:53])[CH3:52])=[C:25]([C@@H:27]3[O:44][C@H:43]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]3[O:29][C:30](=[O:32])[CH3:31])[CH:26]=2)=[CH:18][CH:17]=1.CN1CCOCC1.[CH2:64]([OH:71])[C:65]([NH2:70])([CH2:68][OH:69])[CH2:66][OH:67]>C(OCC)(=O)C.CN(C)C=O.C(Cl)(Cl)Cl>[C:30]([O:29][C@@H:28]1[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@@H:43]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[O:44][C@H:27]1[C:25]1[CH:26]=[C:21]([CH2:20][C:19]2[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][NH:13][C:1]([NH:70][C:65]([CH2:68][OH:69])([CH2:66][OH:67])[CH2:64][OH:71])=[O:2])=[CH:56][CH:55]=2)[C:22]([CH3:54])=[CH:23][C:24]=1[O:50][C:51](=[O:53])[CH3:52])(=[O:32])[CH3:31]

Participants

8

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 79724-MethylmorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 67303976HCID 67303976, compound

Product 1

HCID 67304415HCID 67304415, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a chloroform solution (300 μL) of 1,1′-carbonyldiimidazole (7.30 mg, 0.045 mmol) were added a chloroform solution (150 μL) of (1S)-1-[5-[4-(2-aminoethyl)benzyl]-2-acetoxy-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-acetyl-D-glucitol (18.4 mg, 0.030 mmol) and N-methyl morpholine (4.95 μL, 0.045 mmol), and the mixture was stirred for 30 minutes at room temperature. After that, to this reaction solution were added tris(hydroxymethyl)aminomethane (10.9 mg, 0.09 mmol) and N,N-dimethylformamide (150 μL), and this reaction mixture was stirred at 60° C. overnight. After the reaction mixture was cooled to room temperature, ethyl acetate was added thereto. And the mixture was washed with water, 1 M hydrochloric acid, and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (chloroform:methanol=95:5) to obtain the title compound (7.9 mg, 35%) as a colorless amorphous compound.

Workup

  1. stirringthis reaction mixture was stirred at 60° C. overnight
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. washAnd the mixture was washed with water, 1 M hydrochloric acid, and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure
  7. customThus obtained residue was purified with silica gel column chromatography (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-56caeeacece84161920f8ee6859b240a
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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