4-Methylmorpholine → HCID 12043645, compound

HRID 1582709Notes

Reaction equation

HRID 1582709 reaction equation
CO[C:3](=[O:24])[C@H:4]([CH2:22][OH:23])[NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1.Cl.COC(=O)[C@H](CO)[NH2:30].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[F:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]3[O:24][CH:3]=[C:4]([C:22]([NH2:30])=[O:23])[N:5]=3)=[CH:12][CH:11]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 54283856HCID 54283856, compound

Product 1

HCID 12043645HCID 12043645, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4-(4-Fluorophenoxy)benzoyl]-L-serine methyl ester. To an ice cold solution of 4-(4-fluorophenoy)benzoic acid (0.79 g, 3.4 mmol), L-serine methyl ester hydrochloride (0.59 g, 3.7 mmol), and a 1-hydroxybenzotriazole hydrate (0.57 g, 3.7 mmol) in DMF (20 mL) was added N-methylmorpholine (82 mL, 7.4 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.72 g, 3.7 mmol). The resulting solution was allowed to warm to room temperature overnight and was then partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate and the combined ethyl acetate layers were washed with water (3×), dried over sodium sulfate, filtered, and evaporated under reduced pressure to give the desired product as an oil. 1H NMR (DMSO-d6): 8.51 (d, J=7.5 Hz, 1H), 7.92 (d, J=8.7 Hz, 2H), 7.28 (t, J=8.4 Hz, 2H), 7.18-7.13 (m, 2H), 7.04 (d, J=9.0 Hz, 2H), 5.06 (t, J=6.3 Hz, 1H), 4.53 (q, J=7.8 Hz, 1H), 3.79 (t, J=5.4 Hz, 2H), 3.71 (s, 3H).

Workup

  1. customwas then partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washthe combined ethyl acetate layers were washed with water (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1d31e6eb2d794d6b8faae6d7d2986ead
Source dataset
uspto-grants-2004_05
Patent number
US06737418B2

Reaction notes

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