Sodium Bicarbonate → methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2H-pyrazol-3-yl)-2-vinylbenzoate

HRID 595107Notes

Reaction equation

HRID 595107 reaction equation
[C:1]([O:5][C:6]([N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH:19]=[CH2:20])[C:12]([C:21]2[N:22](C3CCCCO3)[N:23]=[CH:24][CH:25]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+]>Cl.CO>[C:35]([O:34][C:32]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH:19]=[CH2:20])[C:12]([C:21]2[NH:22][N:23]=[CH:24][CH:25]=2)=[CH:11][CH:10]=1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86712818methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-[2-(tetrahydropyran-2-yl)-2H-pyrazol-3-yl]-2-vinylbenzoate2×

Product 1

HCID 86712817methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2H-pyrazol-3-yl)-2-vinylbenzoateYield 108.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-[2-(tetrahydropyran-2-yl)-2H-pyrazol-3-yl]-2-vinylbenzoate (Intermediate 10, 2.6 g) and concentrated hydrochloric acid (3 drops) in methanol (80 mL) was stirred at room temperature for 30 minutes. The solution was treated with saturated aqueous sodium bicarbonate solution and the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water and the organic layer was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2H-pyrazol-3-yl)-2-vinylbenzoate (2.38 g) as a white solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5bb85a3c244a49288c6c8dd87f66ba39
Source dataset
uspto-grants-2016_01
Patent number
US09242997B2

Reaction notes

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