4-Methylmorpholine → HCID 21836510, compound

HRID 1739745Notes

Reaction equation

HRID 1739745 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][NH:22][CH2:23][CH2:24][OH:25].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>ClCCl>[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:9][CH:10]([C:12](=[O:14])[N:22]([CH2:23][CH2:24][OH:25])[CH3:21])[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 80162-(Methylamino)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27354401-(Diphenylmethyl)azetidine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 21836510HCID 21836510, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-diphenylmethylazetidine-3-carboxylic acid (see Preparation 58) (1.8 g, 6.73 mmol), 2-methylaminoethanol (0.76 g, 1.5 mol. equiv.), 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride (1.27 g, 1.1 mol. equiv.), 1-hydroxybenzotriazole hydrate (1.08 g, 1.05 mol. equiv.) and N-methylmorpholine (1.5 g, 2.2 mol. equiv.) in dry dichloromethane (50 ml) was stirred at room temperature for sixteen hours. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate solution (50 ml). The layers were separated and the aqueous layer further extracted with ethyl acetate (30 ml). The combined organic layers were dried over anhydrous sodium sulphate. The solution was filtered, the solvent removed from the filtrate under reduced pressure and the residue chromatographed using silica gel eluting with methanol:dichloromethane (7:93, by volume) to give the title compound (1.76 g). TLC Rf 0.3 (silica, methanol:dichloromethane, 7:93, by volume). LRMS m/z=325(m+1)+. Found C, 71.99; H, 7.60; N, 8.47. C20H24N2O2.0.13 CH2Cl2 requires C, 72.14; H, 7.30; N, 8.36%.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate solution (50 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer further extracted with ethyl acetate (30 ml)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  6. filtrationThe solution was filtered
  7. customthe solvent removed from the filtrate under reduced pressure
  8. customthe residue chromatographed

Sources & evidence

ORD record
ord-a16276f098c64d8aab411cff741c3a86
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

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