4-Methylmorpholine → N-[[1,2,3,4-Tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

HRID 1656056Notes

Reaction equation

HRID 1656056 reaction equation
[C:1]([C:4]1([CH2:14][S:15][C:16](=[O:18])[CH3:17])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([OH:3])=O.CN1CCOCC1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:37]([O:44][C:45](=[O:50])[CH:46]([OH:49])[CH2:47][NH2:48])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:16]([S:15][CH2:14][C:4]1([C:1]([NH:48][CH2:47][CH:46]([C:45]([O:44][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:50])[OH:49])=[O:3])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 197899352-Carboxy-2-[(acetylthio)methyl]-1,2,3,4-tetrahydronaphthaleneHCID 88125266Isoserine benzyl ester tosylate salt

Product 1

HCID 88127936N-[[1,2,3,4-Tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 2-carboxy-2-[(acetylthio)methyl]-1,2,3,4-tetrahydronaphthalene (2.88 g, 10.0 mmol) in dry dimethylformamide (20 mL). To this solution add N-methyl morpholine (1.01 g, 10.0 mmol), isoserine benzyl ester tosylate salt (3.67 g, 10.0 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.92 g, 10.0 mmol). Stir the reaction mixture for 18 hours under an atmosphere of argon at ambient temperature then partition between ethyl acetate and dilute HCl. Wash the organic solution with water, saturated sodium hydrogen carbonate then brine. Dry the solution (MgSO4) and concentrate in vacuo. Purify the residue by column chromatography (ethyl acetate:hexane) to give the title compound.

Workup

  1. customthen partition between ethyl acetate and dilute HCl
  2. washWash the organic solution with water, saturated sodium hydrogen carbonate
  3. dry with materialDry the solution (MgSO4)
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-abd1491b6eac43038c4de47262fb2b6e
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Reaction notes

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