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Dichloromethane → HCID 24812203, compound

HRID 1945463
Notes
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Reaction equation

HRID 1945463 reaction equation
[C:1]12([C:11]3[CH:22]=[CH:21][C:14]([O:15][CH2:16][CH2:17]C(O)=O)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:23][O:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([NH2:33])[CH:27]=1.ClCCl.[OH-].[Na+]>C[Si](OP(=O)=O)(C)C>[CH3:23][O:24][C:25]([C:26]1[CH:31]=[CH:30][C:29]2[O:32][C:17]([CH2:16][O:15][C:14]3[CH:13]=[CH:12][C:11]([C:1]45[CH2:10][CH:5]6[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]6)[CH2:2]4)[CH2:8]5)=[CH:22][CH:21]=3)=[N:33][C:28]=2[CH:27]=1)=[O:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 14798Sodium HydroxideHCID 16772355(4-Adamantan-1-yl-phenoxymethyl)acetic acid

Product 1

HCID 24812203HCID 24812203, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 16133246
Trimethyl(phosphooxy)silane
Solvent

Conditions

Temperature
140 °C

Procedure

A mixture of (4-adamantan-1-yl-phenoxymethyl)-acetic acid (200.0 mg, 0.70 mmol) and 3-amino-4-hydroxy-benzoic acid methyl ester (164.3 mg, 0.98 mmol) in PPSE (3 mL) was heated at 140° C. for 2 h. At the end of the reaction period, the mixture was taken to dichloromethane and neutralized with 1 N NaOH solution. The organic layer was separated and the aqueous solution extracted with dichloromethane. The combined extracts were dried over anhydrous MgSO4, filtered and the solvent was removed with rotary evaporator under reduced pressure. The residue was purified by flash chromatography (n-Hexane:EtoAc:MeOH=6:3:1) to afford 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid methyl ester as a white solid (187.3 mg, 64.1% yield).

Workup

  1. customAt the end of the reaction period
  2. customThe organic layer was separated
  3. extractionthe aqueous solution extracted with dichloromethane
  4. dry with materialThe combined extracts were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed with rotary evaporator under reduced pressure
  7. customThe residue was purified by flash chromatography (n-Hexane:EtoAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-c8c6abfa0e8642a8ae145363186a44ef
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394799B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes