1,2-Dichloroethane → (1S,2S)-2-(5-cyclohexylcarbamoyl)pentanoylamino-3-morpholino-1-phenyl-1-propanol

HRID 2186656Notes

Reaction equation

HRID 2186656 reaction equation
[CH:1]1([NH:7][C:8]([CH2:10][CH2:11][CH2:12][CH2:13]C(O)=O)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:19]([CH2:22]C)CC)C.C(Cl)CCl.N[C@@H:29]([CH2:38][N:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1)[C@H:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[OH:31].C[OH:46]>C(Cl)Cl>[CH2:3]1[CH2:2][CH:1]([NH:7][C:8]([C@H:10]([CH2:11][CH2:12][CH3:13])[C:22]([NH:19][C@:30]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([OH:31])[CH2:29][CH2:38][N:39]2[CH2:40][CH2:41][O:42][CH2:43][CH2:44]2)=[O:46])=[O:9])[CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 887MethanolHCID 8471TriethylamineHCID 10513992(1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanolHCID 224484036-(Cyclohexylamino)-6-oxohexanoic acid

Product 1

HCID 69821349(1S,2S)-2-(5-cyclohexylcarbamoyl)pentanoylamino-3-morpholino-1-phenyl-1-propanolYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixed solvent of methylene chloride:methanol=4:1 (10 ml), 5-cyclohexylcarbamoylpentanoic acid (546.0 mg, 2.4 mmol), triethylamine (620 μl, 4.4 mmol) and EDC (460 mg, 2.4 mmol) were added to (1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanol (472.0 mg, 2.0 mmol), followed by stirring overnight. Methylene chloride (100 ml) was added to the reaction solution. After washed with a saturated sodium hydrogen carbonate solution (50 ml), water (50 ml) and saturated brine (50 ml) successively, the organic layer was dried over sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the title compound (607 mg, yield 68.0%) as colorless oil.

Workup

  1. washAfter washed with a saturated sodium hydrogen carbonate solution (50 ml), water (50 ml) and saturated brine (50 ml) successively
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-b54169715d0048df991a09d8ca586ae2
Source dataset
uspto-grants-2002_06
Patent number
US06407064B2

Reaction notes

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