4-Methylmorpholine → HCID 19065073, compound

HRID 482004Notes

Reaction equation

HRID 482004 reaction equation
[CH3:1][CH2:2]N=C=NCCCN(C)C.Cl.[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:23]=1[O:24][CH2:25][C:26]([OH:28])=O)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1C=CC2N(O)N=[N:40]C=2C=1.Cl.C(N)C.CN1CCOCC1>CN(C=O)C>[CH2:1]([CH:25]([O:24][C:23]1[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:22]=1[CH2:21][NH:20][C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[C:26]([NH2:40])=[O:28])[CH3:2]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 540723652-[4-Chloro-2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenoxy]acetic acid

Product 1

HCID 19065073HCID 19065073, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC Hydrochloride (249 mg, 1.3 mmol) was added to a stirred mixture of 2-t-butoxycarbonylaminomethyl-4-chlorophenoxyacetic acid (316 mg, 1.0 mmol), HOBT (176 mg, 1.3 mmol), ethylamine hydrochloride (106 mg, 1.3 mmol) and N-methylmorpholine (0.396 ml, 3.6 mmol) in DMF (4 ml) and the mixture was stirred for 16 h. The reaction was partitioned between ethylacetate and 5% KHSO4 solution and the organic layer was washed with 5% KHSO4 solution, water, NaHCO3 solution and brine, dried (Na2SO4) and evaporated in vacuo to a solid (333 mg) which was used for the next step.

Workup

  1. customThe reaction was partitioned between ethylacetate and 5% KHSO4 solution
  2. washthe organic layer was washed with 5% KHSO4 solution, water, NaHCO3 solution and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo to a solid (333 mg) which

Sources & evidence

ORD record
ord-ce6fb1e6bd584ae6974f8f60ba16b189
Source dataset
uspto-grants-1998_08
Patent number
US05792779

Reaction notes

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