Phosphonic acid, P-(3-aminophenyl)- → N5-(3-phosphonophenyl)-L-glutamine

HRID 330860

Reaction equation

HRID 330860 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:8]([O:10]C(C)(C)C)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])O.C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:56][C:57]1[CH:58]=[C:59]([P:63](=[O:66])([OH:65])[OH:64])[CH:60]=[CH:61][CH:62]=1>CN(C=O)C.C(N(CC)CC)C>[P:63]([C:59]1[CH:58]=[C:57]([NH:56][C:5](=[O:7])[CH2:4][CH2:3][C@@H:2]([C:8]([OH:10])=[O:9])[NH2:1])[CH:62]=[CH:61][CH:60]=1)([OH:66])([OH:65])=[O:64]

Participants

7

Reactant 4

HCID 79477Phosphonic acid, P-(3-aminophenyl)-HCID 181649HOAtHCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 45275687N5-(3-phosphonophenyl)-L-glutamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Boc-Glu-OtBu (236 mg, 0.78 mmol), HOAt (127 mg, 0.936 mmol) and HATU (356 mg, 0.936 mmol) were dissolved in 1 ml of DMF, and triethylamine (0.21 ml) was added to the solution. Ten minutes after, the crude product of (3-aminophenyl)phosphonic acid was added and stirred at room temperature overnight. The solvent was distilled off and the mixture was purified in accordance with the purification step A to give the title compound.

Workup

  1. distillationThe solvent was distilled off
  2. customthe mixture was purified in accordance with the purification step A

Sources & evidence

ORD record
ord-9589b3b1f96b49b2b6552322e85ab6d2
Source dataset
uspto-grants-2014_11
Patent number
US08877739B2

Linked notes

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