Actarit → Boc-aminopropanol actarit

HRID 1359990

Reaction equation

HRID 1359990 reaction equation
[C:1]([O:5][C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.[CH3:18][C:19]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][C:29]([OH:31])=[O:30])=[CH:26][CH:27]=1)=[O:20].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7].[CH3:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([OH:31])=[O:30])=[CH:24][CH:23]=1)=[O:20]

Participants

8

Reactant 4

HCID 2018ActaritHCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 86623043Boc-aminopropanol actaritYield 83%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 2 ml of dichloromethane, 123.1 mg (0.703 mmol) of the Boc-aminopropanol obtained in Reference Example 1 was dissolved, and then a DMF solution (1 ml) of 136.0 mg (0.704 mmol) of actarit was added thereto, and 17.1 mg (0.140 mmol) of DMAP and 175.4 mg (0.915 mmol) of WSCI.HCl were added thereto in this order under ice-cooling, followed by stirring overnight while gradually returning to room temperature. Ethyl acetate was added thereto, followed by separation by washing with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively. After dehydration drying with sodium sulfate, ethyl acetate was evaporated under reduced pressure. The precipitate was purified by silica gel column chromatography to give 203.1 mg (83%) of the titled compound. The structure was identified by 1H-NMR.

Workup

  1. dissolutionwas dissolved
  2. temperaturein this order under ice-cooling
  3. customwhile gradually returning to room temperature
  4. customfollowed by separation
  5. washby washing with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively
  6. dry with materialAfter dehydration drying with sodium sulfate, ethyl acetate
  7. customwas evaporated under reduced pressure
  8. customThe precipitate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-31cb5099ca0740c893807ef3f604837f
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Linked notes

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