Hydrochloric Acid → HCID 44427073, compound

HRID 2233066Notes

Reaction equation

HRID 2233066 reaction equation
C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3=[CH:17][C:18]4[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=4[CH:24]=[C:15]3[N:14]([CH3:29])[C:13]3[CH:30]=[CH:31][C:32](B4OC(C)(C)C(C)(C)O4)=[CH:33][C:12]=3[N:11]=2)=[CH:6][CH:5]=1.[OH-].[Na+].Cl.C1C[O:50][CH2:49][CH2:48]1.CO>>[C:49]([C:32]1[CH:31]=[CH:30][C:13]2[N:14]([CH3:29])[C:15]3[C:16]([C:10]([C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:43])=[CH:5][CH:6]=4)=[N:11][C:12]=2[CH:33]=1)=[CH:17][C:18]1[C:19]([CH3:27])([CH3:28])[CH2:20][CH2:21][C:22]([CH3:25])([CH3:26])[C:23]=1[CH:24]=3)(=[O:50])[CH3:48]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 68466574HCID 68466574, compound

Product 1

HCID 44427073HCID 44427073, compound

Procedure

A solution of 4-[5,7,7,10,10-pentamethyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-7,8,9,10-tetrahydro-5H-5,13diazabenzo[4,5]cyclohepta[1,2-b]naphthalen-12-yl]benzoic acid methyl ester (19) (R4=CH3, Z=H, R5=CH3, 0.90 mmol) in THF/MeOH (3:1, 4 mL) is treated with 1 N NaOH (1 mL) and the mixture is stirred for 12 h. The mixture is poured into 1 N HCl and extracted with EtOAc. The extract is washed with brine, dried over MgSO4 and evaporated in vacuo. The resulting solids are collected by filtration and washed with ether/hexane (1:10) to give the benzoic acid (20) (R4=CH3, Z=H, R5=CH3) as yellow solid:

Workup

  1. extractionextracted with EtOAc
  2. washThe extract is washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. filtrationThe resulting solids are collected by filtration
  6. washwashed with ether/hexane (1:10)

Sources & evidence

ORD record
ord-81d6761ddfe34f70bf91d0380f6c9854
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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