Hydrochloric Acid → (S,S)-2,7-Diamino-(Z)-oct-4-ene-1,8-dioic acid dimethylester

HRID 976014Notes

Reaction equation

HRID 976014 reaction equation
COC1[C@@H](C(C)C)N=[C:6]([O:26]C)[C@H:7]([CH2:9]/[CH:10]=[CH:11]\[CH2:12][C@H:13]2[C:18]([O:19][CH3:20])=N[C@H](C(C)C)C(OC)=[N:14]2)[N:8]=1.Cl.CC#N.[CH3:35][OH:36].[O:37]1CCOCC1>O>[CH3:35][O:36][C:6](=[O:26])[C@@H:7]([NH2:8])[CH2:9]/[CH:10]=[CH:11]\[CH2:12][C@H:13]([NH2:14])[C:18]([O:19][CH3:20])=[O:37]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6342AcetonitrileHCID 312751,4-DioxaneHCID 676524241,4-Bis((2R,5S)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)-(Z)-but-2-ene

Product 1

HCID 86750551(S,S)-2,7-Diamino-(Z)-oct-4-ene-1,8-dioic acid dimethylester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,4-Bis((2R,5S)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)-(Z)-but-2-ene (0.58 g, 1.23 mmol) was dissolved in dioxane (8 ml), and 0.25M HCl (8 ml, 2.5 mmol) was added and stirred overnight at ambient temperature. TLC(MeCN:MeOH:H2O/4:1:1). The solution was extracted with diethyl ether, and the aqueous phase was evaporated. The residue was dissolved in a small amount of water, and aqueous ammonia solution was added until a pH of 9 was reached. The aqueous phase was extracted twice with diethyl ether, and the organic phase was dried over MgSO4 and evaporated.

Workup

  1. extractionThe solution was extracted with diethyl ether
  2. customthe aqueous phase was evaporated
  3. dissolutionThe residue was dissolved in a small amount of water, and aqueous ammonia solution
  4. additionwas added until a pH of 9
  5. extractionThe aqueous phase was extracted twice with diethyl ether
  6. dry with materialthe organic phase was dried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-948eafc57b9e411fbf4c5f55e29736df
Source dataset
uspto-grants-1997_03
Patent number
US05610141

Reaction notes

Loading…