2-Aminopyridine → Cervinomycin A2

HRID 2275969Notes

Reaction equation

HRID 2275969 reaction equation
[CH3:1][C:2]12[O:38][CH2:37][CH2:36][N:35]1[C:33](=[O:34])[C:5]1[C:6]([OH:32])=[C:7]3[C:13]4[C:14]([C:16]5[C:27](=[O:28])[C:26]6[C:21](=[CH:22][C:23]([O:30][CH3:31])=[C:24]([OH:29])[CH:25]=6)[O:20][C:17]=5[C:18](=[O:19])[C:12]=4[CH:11]=[CH:10][C:8]3=[CH:9][C:4]=1[CH2:3]2)=[O:15].[CH:39]12CC(C=C1)C1C(OC(=O)C21)=O.NC1C=CC=CN=1.CN(C1C=CC=CN=1)C.CC1(O)C2CC3CC(CC1C3)C2>C(OCC)(=O)C.O.O1CCCC1>[CH3:1][C:2]12[O:38][CH2:37][CH2:36][N:35]1[C:33](=[O:34])[C:5]1[C:6]([OH:32])=[C:7]3[C:13]4[C:14]([C:16]5[C:27](=[O:28])[C:26]6[C:21](=[CH:22][C:23]([O:30][CH3:31])=[C:24]([O:29][CH3:39])[CH:25]=6)[O:20][C:17]=5[C:18](=[O:19])[C:12]=4[CH:11]=[CH:10][C:8]3=[CH:9][C:4]=1[CH2:3]2)=[O:15]

Participants

9

Reactant 5

HCID 104392-AminopyridineHCID 13223826-62-0HCID 218852-DimethylaminopyridineHCID 1365452-Methyl-2-adamantanolHCID 308718218-O-demethyl cervinomycin A2

Product 1

HCID 134061Cervinomycin A2

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

16.42 parts of the compound (II-167-a) (5-norbornene-2,3-dicarboxylic acid anhydride, Wako Pure Chemical Industries, Ltd.) and 53.29 parts of tetrahydrofuran were charged, stirred at 23° C. to dissolved. To the obtained mixture, 2.44 parts of amino pyridine was added at 23° C., and stirred. To the obtained mixture, 2.44 parts of dimethylamino pyridine was added at 23° C., and stirred for 30 minutes at 50° C. To the obtained mixture, a mixture of 16.63 parts of 2-methyl-2-adamantanol and 53.29 parts of tetrahydrofuran was added in the form of drops over 1 hour, and stirred for 10 hours at 50° C. To the obtained mixture, 30 parts of ion-exchanged water and 60 parts of ethyl acetate were added to wash, and separated to collect an organic layer. To the obtained organic layer, 30 parts of ion-exchanged was added to wash, and separated to collect an organic layer. This washing with water operation was repeated three times. The obtained organic layer was concentrated to obtain a concentrate. The concentrate was column-fractionated under the condition below, whereby giving 25.2 parts of the compound (II-167-b).

Workup

  1. dissolutionto dissolved
  2. stirringstirred
  3. stirringstirred for 30 minutes at 50° C
  4. additionwas added in the form of drops over 1 hour
  5. stirringstirred for 10 hours at 50° C
  6. washto wash
  7. customseparated
  8. customto collect an organic layer
  9. additionTo the obtained organic layer, 30 parts of ion-exchanged was added
  10. washto wash
  11. customseparated
  12. customto collect an organic layer
  13. concentrationThe obtained organic layer was concentrated
  14. customto obtain a concentrate

Sources & evidence

ORD record
ord-23cb3e5b28444485aa6ab7bb8ee0f146
Source dataset
uspto-grants-2015_09
Patent number
US09128373B2

Reaction notes

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