Triethylamine → HCID 11667979, compound

HRID 1677597Notes

Reaction equation

HRID 1677597 reaction equation
[CH:1](=[C:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:18])[C:15]([OH:17])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:26][C:27]1[CH:36]=[CH:35][C:30]2[NH:31][C:32](=[O:34])[O:33][C:29]=2[CH:28]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[CH:1](=[C:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:18])[C:15]([NH:26][C:27]2[CH:36]=[CH:35][C:30]3[NH:31][C:32](=[O:34])[O:33][C:29]=3[CH:28]=2)=[O:17])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8269896-amino-1,3-benzoxazol-2(3H)-oneHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 59864376HCID 59864376, compound

Product 1

HCID 11667979HCID 11667979, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 49 mg (0.2 mmol) of (4-benzylidene-piperidine-1-yl)-oxo-acetic acid, 33 μl (0.24 mmol) of triethylamine, 30 mg (0.2 mmol) of 6-amino-3H-benzoxazol-2-one [J. Chem. Soc., 321. (1938)] 79.6 mg (0.21 mmol) of HBTU [O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (Advanced Chem. Tech.)]and 1 ml of dimethylformamide is stirred at room temperature for 24 h. The reaction mixture is purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and toluene:methanol=4:1 as eluent. The quality and the quantity of the product are determined by HPLC-MS method as described above. k′=9.66.

Workup

  1. customThe reaction mixture is purified by column chromatography

Sources & evidence

ORD record
ord-2e792625a3f5478d8f664f130a388f45
Source dataset
uspto-grants-2011_08
Patent number
US08008326B2

Reaction notes

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