4-Methylmorpholine → HCID 131719430, compound

HRID 1683341Notes

Reaction equation

HRID 1683341 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 0.5 N 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 0.5 N 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-8e148abe18ac4187b60dc8bd34d35c24
Source dataset
uspto-grants-1997_06
Patent number
US05637698

Reaction notes

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