Diethyl Ether → HCID 86623035, compound

HRID 1359982Notes

Reaction equation

HRID 1359982 reaction equation
C([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])(OC(C)(C)C)=O.[OH:13][C:14]([CH2:16][C:17]1[CH:28]=[CH:27][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:19][CH:18]=1)=[O:15].[ClH:29].C(OCC)(=O)C.C(OCC)C>ClCCl>[NH2:12][CH:8]([OH:11])[CH2:9][CH3:10].[ClH:29].[OH:15][C:14]([CH2:16][C:17]1[CH:28]=[CH:27][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:19][CH:18]=1)=[O:13]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 21866389Hydrogen chloride-ethyl acetateHCID 86623034HCID 86623034, compound2×

Product 1

HCID 86623035HCID 86623035, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The Boc-aminopropanol-felbinac obtained above (1.69 mmol) was dissolved in dichloromethane (1 ml), and 4 N hydrochloric acid/ethyl acetate (3 ml) was added thereto under ice-cooling. The mixture was returned to room temperature, followed by stirring for 2 hours. After confirming disappearance of Boc-aminopropanol-felbinac by TLC, diethyl ether was added thereto and the thus formed precipitate was centrifuged. The thus obtained precipitate was subjected to three times of decantation with diethyl ether and then dried under reduced pressure to give the titled compound (511.7 mg, yield 99%). The structure was identified by 1H-NMR (CDCl3:CD3OD=1:1).

Workup

  1. temperatureunder ice-cooling
  2. customwas returned to room temperature
  3. additionwas added
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ba07d0bb06f347d5aa7dc0d69e6632d7
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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