4-Methylmorpholine → HCID 22875131, compound

HRID 266904Notes

Reaction equation

HRID 266904 reaction equation
[N:1]1([C:15]([C@H:17]([NH:27][C:28](=[O:40])[C:29]([NH:32]C(OC(C)(C)C)=O)([CH3:31])[CH3:30])[CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:16])[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][CH2:7]2)[CH2:3][CH2:2]1.CN1CCOCC1.[CH2:48]([S:50](Cl)(=[O:52])=[O:51])[CH3:49]>ClCCl>[CH2:48]([S:50]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4]2([CH2:5][CH2:6][N:1]([C:15]([C@H:17]([NH:27][C:28](=[O:40])[C:29]([NH2:32])([CH3:30])[CH3:31])[CH2:18][O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:16])[CH2:2][CH2:3]2)[CH2:7]1)(=[O:52])=[O:51])[CH3:49]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 11667Ethanesulfonyl chlorideHCID 10626499HCID 10626499, compound

Product 1

HCID 22875131HCID 22875131, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 0.158 g the intermediate from Step B in 5 mL of dichloromethane was added 0.053 mL of N-methylmorpholine, and 0.034 mL of ethanesulfonylchloride and stirred at 0° C. for 30 min and RT for 1 h. The reaction mixture was diluted with an additional 5 mL of dichloromethane and washed with 5 mL of saturated sodium bicarbonate solution, brine (5 mL), dried over MgSO4 and concentrated. Flash chromatography of the residue over 10 g of silica gel with CH2Cl2 -ether (3:1) as eluent gave 0.057 g of the desired product.

Workup

  1. washwashed with 5 mL of saturated sodium bicarbonate solution, brine (5 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6c596c865d14463b988a9e389270860f
Source dataset
uspto-grants-1997_07
Patent number
US05652235

Reaction notes

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