Triethylamine → HCID 86755042, compound

HRID 849550Notes

Reaction equation

HRID 849550 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10](=[O:32])[CH:11]([OH:31])[CH2:12][CH2:13][S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=2)(=[O:16])=[O:15])[CH2:3][CH2:2]1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C>C(Cl)Cl>[CH3:33][S:34]([O:31][CH:11]([C:10]([NH:9][CH2:8][CH2:7][N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)=[O:32])[CH2:12][CH2:13][S:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1)(=[O:16])=[O:15])(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19366850HCID 19366850, compound

Product 1

HCID 86755042HCID 86755042, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part H: A cooled solution of 2.1 g (5 mmol) of N1-(2-morpholinoethyl)-2--hydroxy-4-[(3-phenoxybenzyl)sulfonyl]butanamide from Part G in 55 mL of anhydrous CH2Cl2 was treated with 0.5 mL (0.8 g, 7 mM) of methanesulfonyl chloride, followed by 1.0 mL (0.7 g, 7 mM) of triethylamine. After 1 hour, the reaction was concentrated in vacuo, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with ethyl acetate (1×). The organic layers were combined and washed with brine, dried (MgSO4) and concentrated to yield 2.5 g of 1-[(2-morpholinoethyl)amino]carbonyl-3-[(3-phenoxybenzyl)sulfonyl]propyl methanesulfonate suitable for the next reaction.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (1×)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-13cf781de9914550b82503c580bc608e
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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