Iodoethane → HCID 86717536, compound

HRID 712079Notes

Reaction equation

HRID 712079 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14]([OH:16])=[O:15])[CH2:10]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+].I[CH2:23][CH3:24].[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>CN(C)C=O.C(OCC)(=O)C.C(Cl)Cl>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[NH2:8][C@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14]([O:16][CH2:23][CH3:24])=[O:15])[CH2:10]1

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 1512526(1R,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid

Product 1

HCID 86717536HCID 86717536, compoundYield 46.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (from Acros, 0.46 g, 2.0 mmol) in N,N-dimethylformamide (4.6 mL) was added sodium bicarbonate (0.34 g, 4.0 mmol) and iodoethane (0.64 mL, 8.0 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate then washed with sat. sodium bicarbonate, water (2×) and brine. The organic was dried (Na2SO4), filtered, and concentrated to give the crude ester. To the crude ester was added methylene chloride (3.0 mL) and trifluoroacetic acid (1.0 mL, 13 mmol). The resulting solution was stirred for 1 h, then concentrated and dried in vacuo to give 0.25 g (46%) of the title compound. LCMS calculated for C8H16NO2 (M+H)+: m/z=158.1. Found: 158.1.

Workup

  1. washthen washed with sat. sodium bicarbonate, water (2×) and brine
  2. dry with materialThe organic was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude ester
  6. stirringThe resulting solution was stirred for 1 h
  7. concentrationconcentrated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-f2c83d2463c24f768127c716c4bde516
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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