4-Methylmorpholine → HCID 19366850, compound

HRID 849549Notes

Reaction equation

HRID 849549 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][S:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=1)(=[O:10])=[O:9])[C:3]([OH:5])=O.C1C=CC2N(O)N=NC=2C=1.[NH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.CN1CCOCC1>CN(C=O)C.C(Cl)CCl>[O:41]1[CH2:42][CH2:43][N:38]([CH2:37][CH2:36][NH:35][C:3](=[O:5])[CH:2]([OH:1])[CH2:6][CH2:7][S:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)(=[O:10])=[O:9])[CH2:39][CH2:40]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 19366857HCID 19366857, compound

Product 1

HCID 19366850HCID 19366850, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent2×

Procedure

Part G: A solution of 3.4 g (10 mmol) of 2-hydroxy-4-[(3-phenoxybenzyl)sulfonyl]butanoic acid from Part F and 2.1 g (15 mM) HOBT in 15 mL of anhydrous DMF was cooled in an ice bath and treated with 2.3 g (12 mM) of EDC. After 2 hours, the reaction was treated with a solution of 1.5 g (12 mM) of 4-(2-aminoethyl)morpholine and 3.3 mL (3.1 g, 30 mM) of N-methylmorpholine in 5 mL anhydrous DMF. After stirring for 66 hours, the reaction was concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with saturated sodium bicarbonate solution and brine, dried over MgSO4, and concentrated to yield 3.5 g of crude product. The crude product was chromatographed on silica gel using 5% methanol/ethyl acetate followed by 20% ethanol/THF to yield 2.1 g of N1-(2-morpholinoethyl)-2-hydroxy-4-[(3-phenoxybenzyl)sulfonyl]butanamide suitable for the next reaction.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic layer was washed with saturated sodium bicarbonate solution and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto yield 3.5 g of crude product
  8. customThe crude product was chromatographed on silica gel using 5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-dd849fbfffb140358ef3a18928d06fa2
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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