Diisopropylcarbodiimide → HCID 69202874, compound

HRID 2377236Notes

Reaction equation

HRID 2377236 reaction equation
[O:1]=[C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=O)[C:5]=2[CH2:4][CH2:3]1.C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[NH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>CN(C)C=O>[O:1]=[C:2]1[C:10]2[C:5](=[C:6]([C:11]([NH:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 151417Glycine tert-butyl esterHCID 27960291-Hydroxybenzotriazole hydrateHCID 125422061-Oxo-indan-4-carboxylic acid

Product 1

HCID 69202874HCID 69202874, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 5 (250 mg, 1.42 mmol) in N,N-dimethylformamide (4 mL) was added 1,3-diisopropylcarbodiimide (0.268 mL, 1.70 mmol), 1-hydroxybenzotriazole hydrate (58 mg, 0.4 mmol), and t-butyl glycinate (223 mg, 1.7 mmol). The mixture was stirred at room temperature overnight, quenched with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (50:1) as the mobile phase to provide the desired product. MS (APCI): m/z 290 (M+H)+.

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-111bcd4ac2354ec4951daf1d8c5e4451
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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