Ethyl Acetate → HCID 136359928, compound

HRID 1969900Notes

Reaction equation

HRID 1969900 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17](S(C5C=CC(C)=CC=5)(=O)=O)[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C:5](=[CH:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:4]1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O>C1COCC1.[Cl-].[Na+].O>[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C:5](=[CH:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium Fluoride2×HCID 67216361HCID 67216361, compound

Product 1

HCID 136359928HCID 136359928, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl 2-((cis)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylidene)acetate (1.9 g, 3.85 mmol) in THF (30 mL) at 0° C. was added a solution of TBAF (11.55 mL, 11.55 mmol, 1 M in THF). After about 10 min, TBAF (7.70 mL, 7.70 mmol, 1 M in THF) was added. After about 1 h EtOAc and brine were added to the reaction mixture. After about one h the organic layer was separated, concd in vacuo and purified by flash chromatography on silica gel eluting with EtOAc to afford ethyl 2-((cis)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylidene)acetate (1.3 g, 100%) as a mixture of diastereomers: LC/MS (Table 1, Method a) Rt=1.86-1.90 min; MS m/z: 340 (M+H)+.

Workup

  1. customAfter about one h the organic layer was separated
  2. customconcd in vacuo and purified by flash chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-1df584a307f94d6d997ca7abc3583a88
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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