4-Methylmorpholine → HCID 178456078, compound

HRID 2212253Notes

Reaction equation

HRID 2212253 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[CH:13]1([CH2:19][CH:20]([NH:24][C:25](=[N:27][S:28]([CH3:31])(=[O:30])=[O:29])C)[C:21]([OH:23])=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[NH2:32][C@@H:33]([CH2:45][CH3:46])[CH:34]([C:36]1[O:37][C:38]2[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=2[N:40]=1)[OH:35].CN1CCOCC1>C(Cl)Cl.Cl>[O:37]1[C:38]2[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=2[N:40]=[C:36]1[CH:34]([OH:35])[C@@H:33]([NH:32][C:21](=[O:23])[CH:20]([NH:24][CH:25]=[N:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:19][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[CH2:45][CH3:46]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11665617HCID 11665617, compoundHCID 178465711HCID 178465711, compound

Product 1

HCID 178456078HCID 178456078, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyldimethylaminopropyl carbodiimide hydrochloride (0.198 g, 1.14 mmol), hydroybenzotriazole (0.114 g, 0.742 mmol), 3-cyclohexyl-2-(1-methanesulfonyliminoethylamino)-propionic acid (0.205 g, 0.742 mmol) and 2(S)-amino-1-benzoxazol-2-ylbutan-1-ol (0.153 g, 0.743 mmol) in methylene chloride (6 mL) was cooled in an ice bath and then N-methylmorpholine (0.155 g, 1.55 mmol) was added to the reaction mixture which was then stirred at room temperature for 40 min. The reaction mixture was diluted with ice water and dilute hydrochloric acid and the product extracted with ethyl acetate. The extracts were washed with aqueous sodium bicarbonate, then brine, then dried over magnesium sulfate and evaporated to give of N-[1(S)-(benzoxazol-2-ylhydroxymethyl)propyl]-3-cyclohexyl-2-[(methanesulfonyliminomethyl)-amino]propionamide (0.314 g). Exact mass 464.21. Found: M+H=465.3, M+Na=487.3, M−H=463.1.

Workup

  1. temperaturewas cooled in an ice bath
  2. extractionthe product extracted with ethyl acetate
  3. washThe extracts were washed with aqueous sodium bicarbonate
  4. dry with materialbrine, then dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-200caeb8541c4a5eb246d199e4fe8672
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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