Triethylamine → 2-methoxy-3-(L-gamma-glutamylamino)benzoic acid

HRID 705457Notes

Reaction equation

HRID 705457 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.[NH:35](C(OC(C)(C)C)=O)[C@H:36]([C:42]([O:44]C(C)(C)C)=[O:43])[CH2:37][CH2:38][C:39](=O)[OH:40].Cl.C(N(CC)CC)C.[CH3:64][O:65][C:66]1[C:75]([NH2:76])=[CH:74][CH:73]=[CH:72][C:67]=1[C:68]([O:70]C)=[O:69]>ClCCl>[CH3:64][O:65][C:66]1[C:75]([NH:76][C:39](=[O:40])[CH2:38][CH2:37][C@@H:36]([C:42]([OH:44])=[O:43])[NH2:35])=[CH:74][CH:73]=[CH:72][C:67]=1[C:68]([OH:70])=[O:69]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 13338715Methyl 3-amino-2-methoxybenzoateHCID 131731743Boc-Glu-OtBu hydrochloride

Product 1

HCID 666150812-methoxy-3-(L-gamma-glutamylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

84 mg (0.2 mmol) of HATU, 30 mg (0.2 mmol) of HOAt, 61 mg (0.2 mmol) of Boc-Glu-OtBu hydrochloride, 0.084 mL (0.6 mmol) of triethylamine and 1 mL of dichloromethane were added to 36 mg (0.2 mmol) of methyl 2-methoxy-3-aminobenzoate, and stirred at room temperature overnight.

Sources & evidence

ORD record
ord-7cf33489b77b4c0386b22d44f2f47e3a
Source dataset
uspto-grants-2015_11
Patent number
US09174932B2

Reaction notes

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