4-Methylmorpholine → HCID 22733337, compound

HRID 2084411Notes

Reaction equation

HRID 2084411 reaction equation
[CH2:1]([C:8]1([S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[S:12][C:11](=[O:13])[N:10]([CH2:14][C:15]([OH:17])=O)[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.[CH2:48]([O:55][NH2:56])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH2:1]([C:8]1([S:19]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)(=[O:20])=[O:21])[S:12][C:11](=[O:13])[N:10]([CH2:14][C:15]([NH:56][O:55][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:17])[C:9]1=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10113827HCID 10113827, compound

Product 1

HCID 22733337HCID 22733337, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[5-Benzyl-5-(4-methoxybenzenesulfonyl)-2,4-dioxothiazolidin-3-yl]-acetic acid (Example 27) (0.400 g, 0.92 mmol) in 13 mL of dichloromethane was added 1-hydroxybenzotriazole (0.126 g, 0.93 mmol), 4-methylmorpholine (0.506 g, 5.00 mmol), O-benzylhydroxylamine hydrochloride (0.440 g, 2.76 mmol), and 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.232 g, 1.21 mmol) and the mixture was stirred at room temperature for 24 hours under a nitrogen atmosphere. The mixture was diluted with 50 mL of dichloromethane and washed with 2×100 mL of water. The combined aqueous washings were back extracted with 100 mL of dichloromethane and the combined organic phases were washed with 100 mL of brine, dried over anhydrous Na2SO4 and concentrated in vacuo. Column chromatography provided 0.280 g of 2-[5-Benzyl-5-(4-methoxybenzenesulfonyl)-2,4-dioxothiazolidin-3-yl]-N-benzyloxyacetamide as a colorless foam. This material was dissolved in 25 mL of dioxane and stirred at room temperature under a hydrogen atmosphere with an excess of 10% Pd on carbon for 2 days. The mixture was filtered through a celite pad washing with dioxane, followed by ethyl acetate, then methanol. The combined filtrates were concentrated in vacuo and column chromatography provided 0.050 g of the title compound as a white powder. m.p. 81-85° C.

Workup

  1. washwashed with 2×100 mL of water
  2. extractionThe combined aqueous washings were back extracted with 100 mL of dichloromethane
  3. washthe combined organic phases were washed with 100 mL of brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40c4bd04bec34ea28186a5dc5723c3d4
Source dataset
uspto-grants-2004_04
Patent number
US06716862B2

Reaction notes

Loading…