4-Methylmorpholine → HCID 20058467, compound

HRID 2050557Notes

Reaction equation

HRID 2050557 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=O)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[CH3:37][CH:38]([NH2:45])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>C(OCC)(=O)C>[CH3:37][CH:38]([NH:45][C:16](=[O:18])[CH:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([O:20][CH3:21])[CH:11]=1)[CH3:19])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 127352-OctylamineHCID 62365Isobutyl chloroformateHCID 200584693-Methoxy-α-methyl-4-(phenylmethoxy)benzeneacetic acid

Product 1

HCID 20058467HCID 20058467, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-(4-benzyloxy-3-methoxyphenyl)propionic acid (5.0 g, 17.5 mmoles) and 4-methylmorpholine (2.0 mL, 17.5 mmoles) in ethyl acetate (170 mL) at 0° C. was treated with isobutyl chloroformate (2.26 mL, 17.5 mmoles). The resulting white slurry was stirred for 20 minutes. A solution of racemic 2-octylamine (2.7 g, 21 mmoles) in ethyl acetate (10 mL total solution) was added to the suspension which was then stirred for 3 hours. The mixture was extracted with 1M hydrochloric acid (3×50 mL), with a saturated sodium bicarbonate solution (3×50 mL), with brine (1×50 mL) and dried over magnesium sulfate. The ethyl acetate was rotary evaporated affording N-2-octyl-2-(4-benzyloxy-3-methoxyphenyl)proprionamide as a white solid which was crystallized from ether/methylene chloride to give 4.55 g. This racemic mixture of diastereomers was separated by silica gel chromatography.

Workup

  1. stirringwas then stirred for 3 hours
  2. extractionThe mixture was extracted with 1M hydrochloric acid (3×50 mL), with a saturated sodium bicarbonate solution (3×50 mL), with brine (1×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. customThe ethyl acetate was rotary evaporated

Sources & evidence

ORD record
ord-0fc41069b7164db8b8ae23f64597b449
Source dataset
uspto-grants-1991_05
Patent number
US05013759

Reaction notes

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