Methanol → (S)-2'-amino-3-(3-methoxy-3-methylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol

HRID 1970343Notes

Reaction equation

HRID 1970343 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([OH:25])([CH3:24])[CH3:23])[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([OH:26])=[CH:10][CH:11]=3)[N:6]=1.CO.[CH3:29]S(O)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([O:25][CH3:29])([CH3:23])[CH3:24])[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([OH:26])=[CH:10][CH:11]=3)[N:6]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 11430Potassium CarbonateHCID 67240963(S)-2'-amino-3-(3-hydroxy-3-methylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol

Product 1

HCID 67247848(S)-2'-amino-3-(3-methoxy-3-methylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol

Procedure

A vessel was charged with (S)-2′-amino-3-(3-hydroxy-3-methylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol (0.512 g, 1.457 mmol) in methanol (17.73 mL, 437 mmol). Methane sulfonic acid (0.945 mL, 14.57 mmol) was added, and the vial was sealed and placed in a 55° C. oil bath overnight. Potassium carbonate was added to quench the acid, and the mixture was filtered with the aid of DCM. The filtrate was evaporated, and the residue was soluble in MeOH/DCM, but some potassium carbonate still came through. The residue was purified by chromatography on a 50-g SNAP column, eluting with 0-100% of a 90:10:1 mixture of DCM/MeOH/NH4OH in DCM. The material thus obtained was rechromatographed to under the same conditions to give (S)-2′-amino-3-(3-methoxy-3-methylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol as a pale-yellow solid.

Workup

  1. customthe vial was sealed
  2. customplaced in a 55° C.
  3. customovernight
  4. customto quench the acid
  5. filtrationthe mixture was filtered with the aid of DCM
  6. customThe filtrate was evaporated
  7. customThe residue was purified by chromatography on a 50-g SNAP column
  8. washeluting with 0-100% of a 90:10:1 mixture of DCM/MeOH/NH4OH in DCM
  9. customThe material thus obtained
  10. customwas rechromatographed to under the same conditions

Sources & evidence

ORD record
ord-801537447cc443539bd387fcf7ef4251
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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