4-Methylmorpholine → (S,S)-2-(2-tert-butoxycarbonylamino-pent-4-enoylamino)-3-naphthalen-2-yl-propionic acid methyl ester

HRID 720160Notes

Reaction equation

HRID 720160 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]=[CH2:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][O:17][C:18](=[O:32])[C@@H:19]([NH2:31])[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.CN(C)CCCN=C=NCC>CN(C=O)C>[CH3:16][O:17][C:18](=[O:32])[C@@H:19]([NH:31][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH:14]=[CH2:15])[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2734487(2S)-2-(((tert-butoxy)carbonyl)amino)pent-4-enoic acidHCID 9291934(S)-methyl 2-amino-3-(naphthalen-2-yl)propanoate

Product 1

HCID 25131148(S,S)-2-(2-tert-butoxycarbonylamino-pent-4-enoylamino)-3-naphthalen-2-yl-propionic acid methyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(S)-tert-butoxycarbonylamino-pent-4-enoic acid (3.8 g, 18.0 mmol) and 2-(S)-amino-3-naphthalen-2-yl-propionic acid methyl ester (4.1 g, 18.0 mmol) in DMF (40 mL) are added 1-hydroxybenzotriazole (3.1 g, 23.4 mmol), N-methylmorpholine (9.1 g, 90.0 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (4.5 g, 23.4 mmol) consecutively and the reaction mixture is stirred for 3 hours. The reaction is quenched with aqueous NH4Cl and extracted with ethyl acetate. The extract is dried over Na2SO4, filtered and concentrated in vacuo and the residue purified over silica gel (hexanes/ethyl acetate, 1:1) to afford 6.4 g (84% yield) of the desired product.

Workup

  1. customThe reaction is quenched with aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe residue purified over silica gel (hexanes/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-7941b3db5e9a401ca9f87d0c220fdbb3
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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