Benzyloxycarbonylglycine → HCID 131736174, compound

HRID 1052505Notes

Reaction equation

HRID 1052505 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][N:11]1[CH:15]=[CH:14][C:13]([Br:16])=[C:12]1[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18].[CH2:26]([O:33][C:34]([NH:36][CH2:37][C:38](O)=[O:39])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(OCC)(=O)C>[Br:16][C:13]1[CH:14]=[CH:15][N:11]([NH:10][C:38](=[O:39])[CH2:37][NH:36][C:34](=[O:35])[O:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:12]=1[C:17](=[O:18])[NH:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 14349Benzyloxycarbonylglycine2×HCID 81531Diisopropylethylamine2×HCID 111923Propylphosphonic anhydride2×HCID 70979311HCID 70979311, compound

Product 1

HCID 131736174HCID 131736174, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent4×

Conditions

Temperature
0 °C

Procedure

DIEA (10.5 ml, 60 mmol) was added at 0° C. over a mixture of 1-amino-3-bromo-N-phenyl-1H-pyrrole-2-carboxamide (5.1 g, 18 mmol) and 2-(benzyloxycabonylamino)acetic acid (5.33 g, 25 mmol) in anhydrous ethyl acetate (100 ml). After 15 min T3P® solution (50% AcOEt, 15 ml) was slowly added and stirred 20 min at 0° C. and then at room temperature overnight. Further DIEA (5 ml, 30 mmol), 2-(benzyloxycabonylamino)acetic acid (2.66 g, 25 mmol) and T3P® solution (50% AcOEt, 7 ml) were added and the reaction mixture was stirred at room temperature overnight. More ethyl acetate was added and the reaction crude was washed with water and brine, dried over magnesium sulphate and the solvent was removed under vacuum. The residue was purified by flash chromatography using Isolera® Purification System (0-40%, hexane-AcOEt) to give 7.81 g (41% yield) of the final product with a purity of 45% that was used in the next step without further purification.

Workup

  1. customat room temperature
  2. customovernight
  3. stirringthe reaction mixture was stirred at room temperature overnight
  4. customthe reaction crude
  5. washwas washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent was removed under vacuum
  8. customThe residue was purified by flash chromatography
  9. customIsolera® Purification System (0-40%, hexane-AcOEt)

Sources & evidence

ORD record
ord-29a4e3914499492096d83fc6ec8fa133
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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