Iodoethane → HCID 86743095, compound

HRID 1904161Notes

Reaction equation

HRID 1904161 reaction equation
N12CCCN=C1CCC[CH2:3][CH2:2]2.C(I)C.[C:15]([NH:18][CH2:19][C@@H:20]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[C:21]([OH:23])=[O:22])(=[O:17])[CH3:16].C(NC(NC(OCC1C=CC=CC=1)=O)(C)C(OCC)=O)(=O)C>C(#N)C>[C:15]([NH:18][CH2:19][C@@H:20]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[C:21]([O:23][CH2:2][CH3:3])=[O:22])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54203142HCID 54203142, compoundHCID 86743096HCID 86743096, compound

Product 1

HCID 86743095HCID 86743095, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.45 ml., 3.0 mmole) and ethyl iodide (0.3 ml., 3.75 mmole) are added to a solution of (R)-3-(acetylamino)-2-[[(benzyloxy)carbonyl]amino]propanoic acid (0.7 g., 2.5 mmole) in acetonitrile (15 ml.). The reaction is allowed to stir overnight then concentrated in vacuo. The residue is dissolved in methylene chloride, washed with 2N hydrochloric acid (2×50 ml.), sodium bicarbonate (2×50 ml.), and brine, and then dried over sodium sulfate. The solvent is removed in vacuo and the resulting oil is chromatographed on silica gel eluting with ethyl acetate to yield 0.6 g. of (R)-3-(acetylamino-2-[[(benzyloxy)carbonyl]amino]propanoic acid, ethyl ester as a clear oil.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue is dissolved in methylene chloride
  3. washwashed with 2N hydrochloric acid (2×50 ml.), sodium bicarbonate (2×50 ml.), and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe resulting oil is chromatographed on silica gel eluting with ethyl acetate
  7. customto yield 0.6 g

Sources & evidence

ORD record
ord-dc0db2fad4cc4e70bd138a4b07e3ed0d
Source dataset
uspto-grants-1989_06
Patent number
USH0000642

Reaction notes

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