tert-Butyl isocyanate → HCID 68817483, compound

HRID 736766Notes

Reaction equation

HRID 736766 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH:7]1[NH:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=[C:33]([CH3:41])[CH:32]=2)=[CH:25][CH:24]=1)(=[O:22])=[O:21])=[O:5])C.C(N=C=O)(C)(C)C>C1COCC1>[CH3:41][C:33]1[CH:32]=[C:31]([CH2:30][O:29][C:26]2[CH:27]=[CH:28][C:23]([S:20]([NH:19][CH:7]3[CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10][NH:9][CH2:8]3)(=[O:21])=[O:22])=[CH:24][CH:25]=2)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 68821282HCID 68821282, compound

Product 1

HCID 68817483HCID 68817483, compoundYield 114.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 0.2 g (0.44 mmol) of 3-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester [WO 01/70673, Example 134] in THF (10 mL) at 0° C. was added tert-butylisocyanate (0.130 g, 0.9 mmol). The reaction mixture stirred at 25° C. for 19 h and then the THF was removed in vacuo. The resulting oil was diluted with ethyl acetate (100 mL) and the organics were washed with saturated aqueous sodium chloride (2×30 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column, eluting with an acetonitrile:water gradient, to afford 3-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-4-carboxylic acid as an amorphous white solid (0.23 g, 96%). MS: 556 (M+H)+.

Workup

  1. customthe THF was removed in vacuo
  2. additionThe resulting oil was diluted with ethyl acetate (100 mL)
  3. washthe organics were washed with saturated aqueous sodium chloride (2×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column
  8. washeluting with an acetonitrile

Sources & evidence

ORD record
ord-22b3715f3e98480aa8727cb3f2c95a08
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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