4-Methylmorpholine → HCID 22482947, compound

HRID 1019417Notes

Reaction equation

HRID 1019417 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:25])[CH:5]=[C:6]([NH:8][C:9]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]([C:22](O)=[O:23])([CH3:21])[CH3:20])=[CH:16][CH:17]=2)=[O:10])[CH:7]=1.Cl.C[O:28][C:29](=[O:33])[C@H:30]([CH3:32])[NH2:31].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.CC1C=C(C=C(C)C=1)NC(CC1C=CC(OC(C)(CC)C(O)=O)=CC=1)=O>CN(C)C=O>[CH3:25][C:4]1[CH:5]=[C:6]([NH:8][C:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([CH3:20])([CH3:21])[C:22]([NH:31][CH:30]([CH3:32])[C:29]([OH:28])=[O:33])=[O:23])=[CH:14][CH:13]=2)=[O:10])[CH:7]=[C:2]([CH3:1])[CH:3]=1

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 122335EfaproxiralHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733257Alanine methyl ester hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 15907885HCID 15907885, compound

Product 1

HCID 22482947HCID 22482947, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using RSR13 acid (1.4 g, 4.1 mmol), appropriate (D or L) alanine methyl ester hydrochloride (575 mg, 4.1 mmol) and 1-hydroxybenzotriazole hydrate (610 mg, 4.5 mmol), N-methylmorpholine (622 mg, 6.2 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (946 mg, 4.9 mmol) in dimethylformamide (30 mL), the two isomers were prepared and isolated as described above for compound 21, in 1.67 g yield (98%).

Workup

  1. customthe two isomers were prepared
  2. customisolated
  3. customyield (98%)

Sources & evidence

ORD record
ord-1f77e0fb69db4d18a3c4b563119c38ba
Source dataset
uspto-grants-2002_11
Patent number
US06486342B1

Reaction notes

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