4-Methylmorpholine → HCID 86637807, compound

HRID 425421Notes

Reaction equation

HRID 425421 reaction equation
CN1CCOCC1.[CH2:8]([O:15][C:16]([NH:18][C:19]([CH3:37])([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][N:31]=2)=[CH:26][CH:25]=1)[C:20]([OH:22])=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:38][CH2:39][CH:40]([OH:47])[CH2:41][C:42]([CH3:46])([CH3:45])[CH2:43][CH3:44].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.C(OCC)(=O)C>[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:27]2[CH:26]=[CH:25][C:24]([CH2:23][C:19]([NH:18][C:16](=[O:17])[O:15][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)([CH3:37])[C:20]([NH:38][CH2:39][CH:40]([OH:47])[CH2:41][C:42]([CH3:46])([CH3:45])[CH2:43][CH3:44])=[O:22])=[CH:29][CH:28]=2)=[N:31][CH:32]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 55289824HCID 55289824, compoundHCID 66705683HCID 66705683, compound

Product 1

HCID 86637807HCID 86637807, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-methylmorpholine (186 mg, 1.84 mmol) was added to an ambient temperature solution of 2-{[(benzyloxy)carbonyl]amino}-3-[4-(5-fluoropyridin-2-yl)phenyl]-2-methylpropanoic acid (150 mg, 0.37 mmol), 1-amino-4,4-dimethylhexan-2-ol (214 mg, 1.48 mmol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (84 mg, 0.44 mmol), and 1-hydroxybenzotriazole (67 mg, 0.44 mmol) in methylene chloride (5 mL). After stirring at ambient temperature overnight, the reaction mixture was poured into ethyl acetate and washed successively with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 40-80% ethyl acetate/hexane afforded benzyl {1-[4-(5-fluoropyridin-2-yl)benzyl]-2-[(2-hydroxy-4,4-dimethylhexyl)amino]-1-methyl-2-oxoethyl}carbamate.

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-846a3bd92b254a7fb32064ce2f7ab946
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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