Diisopropylcarbodiimide → HCID 90203307, compound

HRID 624955Notes

Reaction equation

HRID 624955 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][CH:9]1[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25].C(N=C=NC(C)C)(C)C>C1COCC1>[O:25]=[C:20]1[CH2:21][CH2:22][C:23](=[O:24])[N:19]1[O:16][C:15]([CH:9]1[CH2:10][C:11]([CH3:14])([CH3:13])[CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:17]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 222353081-Boc-4,4-dimethyl-pyrrolidine-2-carboxylic acid

Product 1

HCID 90203307HCID 90203307, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,4-dimethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester (2.0 g, 8.22 mmol) in THF (20 mL) was cooled to 0° C. To the cold solution was added N-hydroxysuccinimide (1.2 g, 10.4 mmol) and diisopropylcarbodiimide (1.32 g, 10.4 mmol). Cooling was removed and the mixture stirred for 3 hours at room temperature. The urea was filtered off, washed with diethylether and the filtrates were concentrated. The residue was partitioned between ethyl acetate and cold water; organic phases were washed with cold brine, combined, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/ethyl acetate 9:1) to give the title compound (1.95 g, 70%) as colorless oil; MS (ESI) 341.1 [MH+].

Workup

  1. temperatureCooling
  2. customwas removed
  3. filtrationThe urea was filtered off
  4. washwashed with diethylether
  5. concentrationthe filtrates were concentrated
  6. customThe residue was partitioned between ethyl acetate and cold water
  7. washorganic phases were washed with cold brine
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography (silica, heptane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-c88c26994e13486b80793f3ccaadd2f6
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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