Triethylamine → 2,5-dichloro-3-(L-gamma-glutamylamino)benzoic acid

HRID 2402933Notes

Reaction equation

HRID 2402933 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.[Cl:64][C:65]1[C:74]([NH2:75])=[CH:73][C:72]([Cl:76])=[CH:71][C:66]=1[C:67]([O:69]C)=[O:68]>ClCCl>[Cl:64][C:65]1[C:74]([NH:75][C:39](=[O:40])[CH2:38][CH2:37][C@@H:36]([C:42]([OH:44])=[O:43])[NH2:35])=[CH:73][C:72]([Cl:76])=[CH:71][C:66]=1[C:67]([OH:69])=[O:68]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 23714Chloramben-methylHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131731743Boc-Glu-OtBu hydrochloride

Product 1

HCID 666148192,5-dichloro-3-(L-gamma-glutamylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

190 mg (0.5 mmol) of HATU, 70 mg (0.5 mmol) of HOAt, 152 mg (0.5 mmol) of Boc-Glu-OtBu hydrochloride, 0.21 mL (1.5 mmol) of triethylamine and 2 mL of dichloromethane were added to 110 mg (0.5 mmol) of methyl 2,5-dichloro-3-aminobenzoate, and stirred at room temperature overnight.

Sources & evidence

ORD record
ord-4d5e5e7a55d343eda16c3b1153ae268b
Source dataset
uspto-grants-2014_08
Patent number
US08796485B2

Reaction notes

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