Tetrahydrofuran → HCID 66593356, compound

HRID 1092334Notes

Reaction equation

HRID 1092334 reaction equation
[C:1](C1CCCC1(N)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:17][CH:18]1[CH:25]2[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:27][CH:19]1[CH2:20]3)[CH2:24]2.[CH:28]1[CH:29]=[CH:30][C:31]2N(O)N=[N:34][C:32]=2[CH:33]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C[O:56]CC1>>[C:4]([O:3][C:1](=[O:2])[NH:34][C:32]1([C:33](=[O:56])[NH:17][CH:18]2[CH:19]3[CH2:27][CH:23]4[CH2:22][CH:21]([CH2:26][CH:25]2[CH2:24]4)[CH2:20]3)[CH2:28][CH2:29][CH2:30][CH2:31]1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 253322-AminoadamantaneHCID 757711-HydroxybenzotriazoleHCID 22356033HCID 22356033, compound

Product 1

HCID 66593356HCID 66593356, compound

Procedure

A solution of BOC-1-aminocyclopentane-1-carboxylic acid (882 mg) in dry THF (15 mL) was cooled to 0° C. To this mixture were added 2-aminoadamantane (582 mg), HOBT (519 mg) and DCC (833 mg) sequentially. The mixture was allowed to warm to RT and was then stirred over night. The suspension was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate (20 mL), washed with water, dried over Na2SO4 and evaporated. The crude material was dissolved in ethyl acetate (10 mL) and precipitated with heptane (20 mL) to give the desired material as a colorless solid (1.350 g). MS (ESI): 363.3 (MH+).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (20 mL)
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. dissolutionThe crude material was dissolved in ethyl acetate (10 mL)
  8. customprecipitated with heptane (20 mL)

Sources & evidence

ORD record
ord-70c9e02259424d8aa70aaf9675cd7575
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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