4-Methylmorpholine → HCID 178424138, compound

HRID 59776Notes

Reaction equation

HRID 59776 reaction equation
Cl.[C:2]1([CH3:27])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@@H:19]3[CH2:24][CH2:23][C@H:22]([CH2:25][NH2:26])[CH2:21][CH2:20]3)[CH:14]=2)[O:9]1.[C:28]([O:32][C:33]([NH:35][CH2:36][C:37](O)=[O:38])=[O:34])([CH3:31])([CH3:30])[CH3:29].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.CN1CCOCC1>CN(C)C=O.O>[C:28]([O:32][C:33](=[O:34])[NH:35][CH2:36][C:37](=[O:38])[NH:26][CH2:25][C@H:22]1[CH2:23][CH2:24][C@@H:19]([O:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[O:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:27])[CH2:17][CH2:16]3)[CH2:20][CH2:21]1)([CH3:31])([CH3:29])[CH3:30]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compoundHCID 178424137HCID 178424137, compound

Product 1

HCID 178424138HCID 178424138, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 110 mg of [cis-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexylmethyl]amine hydrochloride (0.28 mmol), 75 mg of N-tert-butoxycarbonylglycine (0.43 mmol), 76 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.40 mmol) and 54 mg of hydroxybenzotriazole (0.40 mmol) at room temperature in 2 ml of dimethylformamide 0.16 ml of N-methylmorpholine (1.42 mmol) were added and stirring at room temperature was continued for 16 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with diluted aqueous sodium carbonate solution, dried with sodium sulfate and filtered, and the solvent removed under reduced pressure. The crude product was purified by column chromatography using ethyl acetate/heptane/methanol 5:10:1 as eluent. 95 mg of the title compound were isolated.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with diluted aqueous sodium carbonate solution
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-560caa57f7c9491789c64d89ccec46d6
Source dataset
uspto-grants-2016_09
Patent number
US09440941B2

Reaction notes

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