N-(tert-butoxycarbonyl)glycine → HCID 66648935, compound

HRID 1898185Notes

Reaction equation

HRID 1898185 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[C:15]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=3)(=[O:19])=[O:18])=[CH:14][C:13]([Cl:31])=[CH:12][N:11]=2)=[O:9])[CH:5]=[CH:4][N:3]=1.[C:32]([NH:39][CH2:40][C:41](O)=[O:42])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].C(N(C(C)C)CC)(C)C.CCCP(=O)=O>C(Cl)Cl.CCOC(C)=O>[C:35]([O:34][C:32](=[O:33])[NH:39][CH2:40][C:41](=[O:42])[NH:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[C:15]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=3)(=[O:19])=[O:18])=[CH:14][C:13]([Cl:31])=[CH:12][N:11]=2)=[O:9])[CH:5]=[CH:4][N:3]=1)([CH3:38])([CH3:36])[CH3:37]

Participants

7

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 57942159HCID 57942159, compound

Product 1

HCID 66648935HCID 66648935, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of N-[2-(2-amino-pyridine-4-carbonyl)-5-chloro-pyridin-3-yl]-4-methyl-3-trifluoromethyl-benzenesulfonamide (800 mg, 1.69 mmol), Boc-glycine (742 mg, 4.24 mmol), diisopropylethylamine (1.9 mL, 10.14 mmol) in methylene chloride (4 mL) was added propylphosphonic anhydride (2.68 mL, 50% solution in EtOAc, 4.24 mmol) was added slowly. The resultant heterogeneous solution was allowed to stir overnight at 45° C. The following day, the reaction was diluted with EtOAc, the organics were washed with saturated sodium bicarbonate, aqueous saturated NH4Cl and dried with sodium sulfate, concentrated in vacuo, and purified via automated silica gel chromatography to provide ({4-[5-chloro-3-(4-methyl-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]-pyridin-2-ylcarbamoyl}-methyl)-carbamic acid tert-butyl ester.

Workup

  1. additionwas added slowly
  2. washthe organics were washed with saturated sodium bicarbonate, aqueous saturated NH4Cl
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified

Sources & evidence

ORD record
ord-33a9b7aa8e36497e802e4e4c1407a8f2
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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