4-Methylmorpholine → HCID 69745735, compound

HRID 720190Notes

Reaction equation

HRID 720190 reaction equation
[NH2:1][CH:2]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[C:12]([NH:14][CH3:15])=[O:13])[CH2:7][CH:6]1[CH2:27][CH3:28])=[O:4].CC(OC([N:44]1[C@H:47]([C:48](O)=[O:49])[CH2:46][CH2:45]1)=O)(C)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C.O.CCOC(C)=O>[CH2:27]([CH:6]1[CH2:7][N:8]([CH:11]([C:12](=[O:13])[NH:14][CH3:15])[CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[CH2:9][CH2:10][N:5]1[C:3](=[O:4])[CH:2]([NH:1][C:48]([CH:47]1[CH2:46][CH2:45][NH:44]1)=[O:49])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[CH3:28]

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2734495(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acidHCID 21901549HCID 21901549, compound

Product 1

HCID 69745735HCID 69745735, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-{4-[2-Amino-3-(4-fluorophenyl)-propionyl]-3-ethyl-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl-propioamide, 41, (0.78 g, 0.83 mmol) and Boc-L-azetidine-2-carboxylic acid (0.17 g, 0.83 mmol), 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide (0.19 g, 1.0 mmol) and 1-hydroxybenzotriazole (0.22 g, 1.66 mmol) are dissolved in anhydrous DMF (2 mL). The reaction mixture is cooled to 0° C., then N-methylmorpholine (0.6 mL, 5.46 mmol) is added. The reaction mixture is stirred for 4 hrs. EtOAc (30 mL) and water (100 mL) are added, and the organic layer is separated. The aqueous layer is extracted with EtOAc (3×30 mL). All organic layers are combined and washed with water (2×50 mL), and dried over Na2SO4. The solution is concentrated in vacuo to afford the desired product which is used without further purification.

Workup

  1. customthe organic layer is separated
  2. extractionThe aqueous layer is extracted with EtOAc (3×30 mL)
  3. washwashed with water (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-1a8374bcb701416987c200ee7c47e329
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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