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4-Methylmorpholine → Methyl-4-{5-[2-(2-anilino-1,3-benzoxazol6-yl)-acetylamino]-2-methoxyphenoxy}-3-methyl-butanoate

HRID 2305622
Notes
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Reaction equation

HRID 2305622 reaction equation
[C:1]1([NH:7][C:8]2[O:9][C:10]3[CH:16]=[C:15]([CH2:17][C:18]([OH:20])=O)[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][CH:22]([CH:27]([O:29][C:30]1[CH:35]=[C:34]([NH2:36])[CH:33]=[CH:32][C:31]=1[O:37][CH3:38])C)[C:23](OC)=O.[OH:39][C:40]1C2N=NNC=2C=CC=1.CN1CC[O:53][CH2:52]C1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[CH3:52][O:53][C:40](=[O:39])[CH2:23][CH:22]([CH3:21])[CH2:27][O:29][C:30]1[CH:35]=[C:34]([NH:36][C:18](=[O:20])[CH2:17][C:15]2[CH:14]=[CH:13][C:11]3[N:12]=[C:8]([NH:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[O:9][C:10]=3[CH:16]=2)[CH:33]=[CH:32][C:31]=1[O:37][CH3:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111498372-Phenylaminobenzoxazol-6-acetic acidHCID 53892958Methyl 2-methyl-3-(2-methoxy-5-aminophenoxy)butyrateHCID 178418300HCID 178418300, compound

Product 1

HCID 54563344
Methyl-4-{5-[2-(2-anilino-1,3-benzoxazol6-yl)-acetylamino]-2-methoxyphenoxy}-3-methyl-butanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-phenylaminobenzoxazole-6-acetic acid(0.067 g), methyl 2-methyl-3-(2-methoxy-5-aminophenoxy)butyrate(0.057 g), hydroxybenzotriazole (0.067 g), and N-methylmorpholine(0.05 ml) in dimethylformamide(0.25 ml) was added 1-(3-dimethylaminopropyl)3-ethylcarbodiimide hydrochloride(0.095 g). The resultant mixture was stirred for 48 hrs then added to water and extracted with ethyl acetate. The organic layer was separated, washed with aqueous acetic acid, brine, aqueous sodium bicarbonate (2 times), dried and evaporated to dryness. The residue was purified by purified by chromatography on silica using an increasingly polar mixture of ethyl acetateldichloromethane and the appropriate fraction yielded, after evaporation to dryness, a solid which was triturated with a mixture of diethylether/hexane to give the product (0.08 g) as a purple-pink solid.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with aqueous acetic acid, brine, aqueous sodium bicarbonate (2 times)
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified
  7. customby purified by chromatography on silica using
  8. additionan increasingly polar mixture of ethyl acetateldichloromethane
  9. customthe appropriate fraction yielded
  10. customafter evaporation to dryness
  11. customa solid which was triturated with a mixture of diethylether/hexane

Sources & evidence

ORD record
ord-40cbb133dd7a46b0b2b9a6dc9d61c7f1
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06441012B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes