Diethyl Ether → HCID 178455994, compound

HRID 1655767Notes

Reaction equation

HRID 1655767 reaction equation
C(OC([N:8]1[C:12]([CH2:13][C@H:14]([N:35]([CH3:45])[C:36](C(OC(C)(C)C)=O)=[O:37])[C:15]([NH:17][C@@H:18]([CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C@@H:19]([OH:27])[CH2:20][C@@H:21]([CH:24]([CH3:26])[CH3:25])[CH:22]=[CH2:23])=[O:16])=[CH:11][N:10]=[CH:9]1)=O)(C)(C)C.CCOCC>Cl.O1CCOCC1>[CH3:45][N:35]([C@@H:14]([CH2:13][C:12]1[N:8]=[CH:9][NH:10][CH:11]=1)[C:15]([NH:17][C@@H:18]([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C@@H:19]([OH:27])[CH2:20][C@@H:21]([CH:24]([CH3:25])[CH3:26])[CH:22]=[CH2:23])=[O:16])[CH:36]=[O:37]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 22847768HCID 22847768, compound

Product 1

HCID 178455994HCID 178455994, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2.1 g of (S)-3-(t-butoxycarbonyl)-α-[1-(t-butoxycarbonyl)-N-methylformamido]-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide were dissolved in 30 ml of 3N hydrogen chloride in dioxan and the mixture was left to stand at room temperature for 5 hours. 500 ml of ether were added and the precipitate formed was filtered off. The precipitate was washed with ether and dissolved in water. Solid sodium bicarbonate was added to the aqueous solution and the mixture was extracted several times with ethyl acetate, to obtain there was obtained 0.85 g of (S)-α-(N-methylformamido)-N-[(1S,2S,4S)-1-(cyclohexyl-methyl)-2-hydroxy-4-isopropyl-5-hexenyl)imidazole-4-propion-amide which was used directly in the next step.

Workup

  1. waitthe mixture was left
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washThe precipitate was washed with ether
  5. dissolutiondissolved in water
  6. additionSolid sodium bicarbonate was added to the aqueous solution
  7. extractionthe mixture was extracted several times with ethyl acetate
  8. customto obtain there

Sources & evidence

ORD record
ord-e5fdb167539f46fe9150e9274e8d201b
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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