Triethylamine → 5-chloro-3-(L-gamma-glutamylamino)benzoic acid

HRID 330866Notes

Reaction equation

HRID 330866 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[CH:66]=[C:67]([NH2:75])[CH:68]=[C:69]([CH:74]=1)[C:70]([O:72]C)=[O:71]>ClCCl>[Cl:64][C:65]1[CH:66]=[C:67]([NH:75][C:39](=[O:40])[CH2:38][CH2:37][C@@H:36]([C:42]([OH:44])=[O:43])[NH2:35])[CH:68]=[C:69]([CH:74]=1)[C:70]([OH:72])=[O:71]

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 52987785Methyl 3-amino-5-chlorobenzoateHCID 131731743Boc-Glu-OtBu hydrochloride

Product 1

HCID 666148435-chloro-3-(L-gamma-glutamylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HATU, 38 mg (0.1 mmol), 14 mg (0.1 mmol) of HOAt, 30 mg (0.1 mmol) of Boc-Glu-OtBu hydrochloride, 0.014 ml (0.1 mmol) of triethylamine and 1 ml of dichloromethane were added to 30 mg (0.1 mmol) of methyl 5-chloro-3-aminobenzoate. The mixture was stirred at room temperature overnight.

Sources & evidence

ORD record
ord-e7fc671e4f714497ad6b80df3557a44b
Source dataset
uspto-grants-2014_11
Patent number
US08877739B2

Reaction notes

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