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

HRID 419175Notes

Reaction equation

HRID 419175 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-03aaf04e6236458b97cd18e8ed5e4e7d
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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