Glycine tert-butyl ester → HCID 69203341, compound

HRID 2377238Notes

Reaction equation

HRID 2377238 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=O)[C:5]2[CH2:6][CH2:7][C:8](=[O:11])[C:9]=2[CH:10]=1.O.ON1C2C=CC=CC=2N=N1.[NH2:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[C:4]([C:12]([NH:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 151417Glycine tert-butyl esterHCID 27960291-Hydroxybenzotriazole hydrateHCID 692008516-Bromo-1-oxo-2,3-dihydro-1H-indene-4-carboxylic acid

Product 1

HCID 69203341HCID 69203341, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 6 (250 mg, 0.98 mmol) in N,N-dimethylformamide (5 mL) was added N-cyclohexylcarbodiimide-N′-methyl polystyrene (761 mg, 1.5 mmol) and 1-hydroxybenzotriazole hydrate (255 mg, 1.7 mmol). The mixture was agitated at room temperature for about 5 minutes, treated with t-butyl glycinate (150 mg, 1.2 mmol), shaken for about 15 hours, and filtered. The filtrate was concentrated under vacuum and the residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (1:1) as the moblie phase to provide the desired product. MS (APCI): m/z 311, 313 (M+H-tBu)+.

Workup

  1. stirringshaken for about 15 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum
  4. customthe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b73d4fe4c6564c5ab33551d58374f672
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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