Water → Benzyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

HRID 1256671Notes

Reaction equation

HRID 1256671 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[C:12]([O:16][C:17](=[O:42])[NH:18][C:19]1[C:20]([NH:31][C:32](=[O:41])[C:33]2[CH:38]=[CH:37][C:36]([CH2:39][NH2:40])=[CH:35][CH:34]=2)=[N:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C.O>C1COCC1>[CH2:5]([O:4][C:2](=[O:3])[NH:40][CH2:39][C:36]1[CH:37]=[CH:38][C:33]([C:32]([NH:31][C:20]2[C:19]([NH:18][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:42])=[CH:24][CH:23]=[C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:21]=2)=[O:41])=[CH:34][CH:35]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 57745571Tert-butyl(2-{[4-(aminomethyl)benzoyl]amino}-6-phenylpyridin-3-yl)carbamate

Product 1

HCID 59627862Benzyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl chloroformate (0.06 ml, 0.420 mmol) was added to a flask containing tert-butyl(2-{[4-(aminomethyl)benzoyl]amino}-6-phenylpyridin-3-yl)carbamate (158 mg, 0.378 mmol) and DIPEA (0.15 ml, 0.859 mmol) in THF (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour. Water was added and the products were extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The organic product was purified by column chromatography on silica gel Biotage 25S, eluting with EtOAc/hexanes (0%-100%) to give a pale slightly yellow transparent gel. MS: cal'd 553 (MH+), exp 553 (MH+).

Workup

  1. extractionthe products were extracted into EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe organic product was purified by column chromatography on silica gel Biotage 25S
  6. washeluting with EtOAc/hexanes (0%-100%)
  7. customto give a pale slightly yellow transparent gel

Sources & evidence

ORD record
ord-0fd74c92c7964037af3eca2bff07ed68
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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