4-Methylmorpholine → HCID 13877874, compound

HRID 256079Notes

Reaction equation

HRID 256079 reaction equation
[NH2:1][CH2:2][CH:3]([S:9][CH2:10][C@@H:11]([C:20]([OH:22])=O)[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:4]1[S:5][CH:6]=[CH:7][CH:8]=1.CN1CCOCC1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(OCC)(=O)C>CN(C)C=O.O>[C:16]([O:15][C:13]([NH:12][C@H:11]1[CH2:10][S:9][CH:3]([C:4]2[S:5][CH:6]=[CH:7][CH:8]=2)[CH2:2][NH:1][C:20]1=[O:22])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 13877868HCID 13877868, compound

Product 1

HCID 13877874HCID 13877874, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 150 g of S-[2-amino-1-(2-thienyl)ethyl]-N-t-butoxycarbonyl-L-cysteine [prepared as described in step (b) above] and 52 ml of N-methylmorpholine in 1 liter of dimethylformamide was added to a solution of 108.4 ml of diphenylphosphoryl azide in 500 ml of dimethylformamide at 10° C., over a period of 4 hours, and the mixture was left to stand at room temperature overnight. At the end of this time, 1.5 liters of ethyl acetate and 1.5 liters of water were added, and the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate, and the resulting extracts were combined with the separated organic layer. The resulting organic mixture was washed twice, each time with an aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate, after which the solvent was evaporated off. The residue was subjected to silica gel column chromatography, using a 1:4 by volume mixture of ethyl acetate and methylene chloride as eluent, to give 112.5 g of the title compound as a gummy substance.

Workup

  1. waitthe mixture was left
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washThe resulting organic mixture was washed twice
  5. dry with materialeach time with an aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  6. customafter which the solvent was evaporated off
  7. additionby volume mixture of ethyl acetate and methylene chloride as eluent

Sources & evidence

ORD record
ord-d6ce5a955c1f4a518c32759a38629797
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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