Hydrochloric Acid → HCID 57929419, compound

HRID 1024110Notes

Reaction equation

HRID 1024110 reaction equation
C1CCN2C(=NCCC2)CC1.[CH3:12][O:13][C:14]([C:16]1[S:17][C:18]([CH2:21][CH2:22][CH2:23][C@@H:24]2[C@@H:28]([C:29]3[CH:34]=[CH:33][C:32]([CH:35]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=4)[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:31][CH:30]=3)[C:27](=[O:51])[CH:26]([O:52][C:53](=[O:55])[CH3:54])[CH:25]2OC(=O)C)=[CH:19][CH:20]=1)=[O:15].Cl>CCOCC>[CH3:12][O:13][C:14]([C:16]1[S:17][C:18]([CH2:21][CH2:22][CH2:23][C@@H:24]2[C@@H:28]([C:29]3[CH:34]=[CH:33][C:32]([CH:35]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=4)[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:31][CH:30]=3)[C:27](=[O:51])[C:26]([O:52][C:53](=[O:55])[CH3:54])=[CH:25]2)=[CH:19][CH:20]=1)=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57929330HCID 57929330, compound

Product 1

HCID 57929419HCID 57929419, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

DBU (15 μL, 0.10 mmol) was added to an ice-cold solution of diacetate 28 (32 mg, 0.048 mmol) in ether (0.5 mL). The solution was stirred at 0° C. for 30 min. and then was allowed to warm to room temperature. After stirring overnight, 1 M HCl was added and the resulting mixture was extracted with ethyl acetate (3×25 mL). The combined organic solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (0%→100% ethyl acetate/hexanes) provided the title compound (21 mg, 71%).

Workup

  1. temperatureto warm to room temperature
  2. stirringAfter stirring overnight
  3. extractionthe resulting mixture was extracted with ethyl acetate (3×25 mL)
  4. washThe combined organic solution was washed with brine
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash chromatography on silica gel (0%→100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b76ec3e928334abface5bb9b8960e114
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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