Sodium Carbonate → HCID 178456018, compound

HRID 1655751Notes

Reaction equation

HRID 1655751 reaction equation
[CH2:1]([C@H:8]([NH:18][C:19]([C@@H:21]([NH:35]C(OC(C)(C)C)=O)[CH2:22][C:23]1[N:24]=[CH:25][N:26](C(OC(C)(C)C)=O)[CH:27]=1)=[O:20])[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl.O1CCOCC1>[NH2:35][C@@H:21]([CH2:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1)[C:19]([NH:18][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:15])[CH3:16])[CH:12]=[CH2:13])=[O:20]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 22847844HCID 22847844, compound

Product 1

HCID 178456018HCID 178456018, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1 g (1.7 mmol) of t-butyl 4-[(S)-2-[[(1S,2S,4S)-1-benzyl-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-(1-t-butoxyformamido)ethyl]imidazole-1-carboxylate were dissolved in 7 ml of 5N hydrogen chloride in dioxane and subsequently stirred at room temperature for 2 hours. Thereafter, the reaction mixture was poured into sodium carbonate solution and extracted with ethyl acetate. The organic extract was dried and evaporated and the residue was chromatographed on silica gel with a 3:1 mixture of methylene chloride and methanol, to obtain 340 mg (52%) of (S)-α-amino-N-[(1S,2S,4S)-1-benzyl-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propion-amide as a foam, MS; 385 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. customwas dried
  4. customevaporated
  5. customthe residue was chromatographed on silica gel with a 3:1 mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-e1f26d9a89e54b5991075648022533db
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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