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Dimethylformamide → (S)-2'-(cyclopropylethynyl)-7'-(2-methoxy-2-methylpropoxy)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335769
Notes
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Reaction equation

HRID 335769 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:25]=1)[C:18]1[CH:17]=[C:16]([C:19]#[C:20][CH:21]3[CH2:23][CH2:22]3)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:24])=[CH:9][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.I[CH2:38][C:39]([O:42][CH3:43])([CH3:41])[CH3:40]>O.CCOC(C)=O>[CH:21]1([C:20]#[C:19][C:16]2[CH:15]=[CH:14][C:13]3[O:12][C:11]4[C:6](=[CH:7][C:8]([O:24][CH2:38][C:39]([O:42][CH3:43])([CH3:41])[CH3:40])=[CH:9][CH:10]=4)[C@:5]4([CH2:4][O:3][C:2]([NH2:1])=[N:25]4)[C:18]=3[CH:17]=2)[CH2:23][CH2:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 189668321-Iodo-2-methoxy-2-methylpropaneHCID 67240959(S)-2-amino-2'-(cyclopropylethynyl)-5H-spiro[oxazole-4,9'-xanthen]-7'-ol

Product 1

HCID 58466161(S)-2'-(cyclopropylethynyl)-7'-(2-methoxy-2-methylpropoxy)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 2-5 mL microwave vial was charged with (S)-2-amino-2′-(cyclopropylethynyl)-5H-spiro[oxazole-4,9′-xanthen]-7′-ol (0.250 g, 0.752 mmol), cesium carbonate (0.980 g, 3.01 mmol), and DMF (3.01 mL). The mixture was stirred vigorously for 5 min, then 1-iodo-2-methoxy-2-methylpropane (0.303 mL, 2.257 mmol) was added via syringe. The vial was sealed and the reaction was microwaved at 110° C. for two hours. The mixture was diluted with water and EtOAc and the layers were separated, and the aqueous layer was extracted twice with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on a 12-g Redi-Sep column, eluting with 0-10% MeOH/DCM to provide (S)-2′-(cyclopropylethynyl)-7′-(2-methoxy-2-methylpropoxy)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as an off-white solid.

Workup

  1. customThe vial was sealed
  2. customthe reaction was microwaved at 110° C. for two hours
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted twice with EtOAc
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on a 12-g Redi-Sep column
  9. washeluting with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-829e75c3867b4877988f7abf68a58a28
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883782B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes