4-Methylmorpholine → HCID 22875136, compound

HRID 266901Notes

Reaction equation

HRID 266901 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][N:13]([C:16]([C@H:18]([NH:28][C:29](=[O:41])[C:30]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])([CH3:32])[CH3:31])[CH2:19][O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:17])[CH2:12][CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1.CN1CCOCC1.[CH3:49][S:50](Cl)(=[O:52])=[O:51]>ClCCl>[CH3:49][S:50]([N:8]1[C:5]2[C:4](=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:10]2([CH2:11][CH2:12][N:13]([C:16]([C@H:18]([NH:28][C:29](=[O:41])[C:30]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])([CH3:32])[CH3:31])[CH2:19][O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:17])[CH2:14][CH2:15]2)[CH2:9]1)(=[O:52])=[O:51]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 22875156HCID 22875156, compound

Product 1

HCID 22875136HCID 22875136, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 0.134 g the intermediate from Step B in 5 mL of dichloromethane was added 0.080 mL of N-methylmorpholine, and 0.022 mL of methanesulfonylchloride and stirred at 0° C. for 30 min. 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 20 g of silica gel gave 0.101 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-c59e8ddbdbac4354aaec171402a37a16
Source dataset
uspto-grants-1997_07
Patent number
US05652235

Reaction notes

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