4-Methylmorpholine → HCID 131719430, compound

HRID 260215Notes

Reaction equation

HRID 260215 reaction equation
Cl.[OH:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([C:9]([O:11][CH3:12])=[O:10])[NH2:8].CN1CCOCC1.[C:20]1(=[O:45])[N:24]([NH:25][C@H:26]([C:37](O)=[O:38])[CH2:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][CH:29]=2)[C:23](=[O:40])[C:22]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:21]12.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(Cl)Cl>[C:23]1(=[O:40])[N:24]([NH:25][C@H:26]([C:37]([NH:8][C@H:7]([C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][OH:2])=[O:38])[CH2:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][CH:29]=2)[C:20](=[O:45])[C:21]2=[CH:44][CH:43]=[CH:42][CH:41]=[C:22]12

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11680005methyl (2S)-2-amino-6-hydroxyhexanoate hydrochlorideHCID 54478215HCID 54478215, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 131719430HCID 131719430, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The above crude 6-hydroxy-L-norleucine, methyl ester, hydrochloride was dissolved in dimethylformamide (6 ml.) and methylene chloride (25 ml.) and treated with 4-methylmorpholine (1.30 ml., 1.20 g., 11.8 mmol.). The solution was cooled to 0° C. and treated with N-phthalimido-L-tryptophan followed by hydroxybenzotriazole (925 mg., 6.8 mmol.) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.438 g., 7.5 mmol.). The mixture was stirred at 0° C. for 0.5 hour and then at room temperature for 2.5 hours. The solution was partitioned between ethyl acetate and water and the organic layer was washed successively with 0.5N hydrochloric acid, water, 5% sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give 3.06 g., of title product as a yellow foam. TLC: (ethyl acetate) Rf =0.35.

Workup

  1. waitat room temperature for 2.5 hours
  2. customThe solution was partitioned between ethyl acetate and water
  3. washthe organic layer was washed successively with 0.5N hydrochloric acid, water, 5% sodium bicarbonate, and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customto give 3.06 g

Sources & evidence

ORD record
ord-6eae64ef1cc4476eaa2cbc0b19db180e
Source dataset
uspto-grants-1996_06
Patent number
US05525723

Reaction notes

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