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Dichloromethane → HCID 24812204, compound

HRID 1945464
Notes
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Reaction equation

HRID 1945464 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]([NH2:32])=[C:28]([OH: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[N: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)[O:33][C:28]=2[CH:27]=1)=[O:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl esterHCID 16772355(4-Adamantan-1-yl-phenoxymethyl)acetic acid

Product 1

HCID 24812204HCID 24812204, compoundYield 63%

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 4-amino-3-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-6-carboxylic acid methyl ester as a white solid (184.0 mg, 63.0% 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-69db9c742e1241f0885b8922924b4842
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