4-Methylmorpholine → 2-bromopentanoyl-(L)-homophenylalanine methyl ester

HRID 276110Notes

Reaction equation

HRID 276110 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:21])[C@H:11]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:12].CN1CCOCC1.[Br:29][CH:30]([CH2:34][CH2:35][CH3:36])[C:31](O)=[O:32].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>CCCCCC.C(OCC)(=O)C.ClCCl>[CH3:8][O:9][C:10](=[O:21])[C@H:11]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:12][C:31](=[O:32])[CH:30]([Br:29])[CH2:34][CH2:35][CH3:36]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 11446Pentanoic acid, 2-bromo-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69963366(l)-Homophenylalanine methyl ester trifluoroacetic acid saltHCID 178418300HCID 178418300, compound

Product 1

HCID 229508312-bromopentanoyl-(L)-homophenylalanine methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

Combine (L)-homophenylalanine methyl ester trifluoroacetic acid salt (3.6 g, 10 mmol), N-methylmorpholine (3.3 mL, 30 mmol), and dichloromethane (20 mL). Add 2-bromovaleric acid (2.0 mL, 15.3 mmol), hydroxybenzotriazole (2.07 g, 15.3 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.93 g, 15.3 mmol). After 1 hour, partition the reaction mixture between methyl t-butyl ether and an aqueous 5% sulfuric acid solution. Separate the layers, extract the organic layer with a saturated sodium bicarbonate solution and then brine. Dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 3/1 hexane/ethyl acetate and then 2.5/1 hexane/ethyl acetate to give the title compound: Rf=0.55 (silica gel, 1/1 ethyl acetate/hexane).

Workup

  1. custompartition the reaction mixture between methyl t-butyl ether
  2. customSeparate the layers
  3. extractionextract the organic layer with a saturated sodium bicarbonate solution
  4. dry with materialDry over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-14be32bc2a4c47c5a16fcb495894ef24
Source dataset
uspto-grants-2002_03
Patent number
US06352976B1

Reaction notes

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