Triethylamine → methyl N-({2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]phenyl}carbonyl)glycinate

HRID 1502210Notes

Reaction equation

C(N(CC)CC)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:41][C:42]1[CH:50]=[CH:49][C:48]([C:51]([C:53]2[N:61]3[C:56]([CH:57]=[CH:58][CH:59]=[CH:60]3)=[C:55]([Br:62])[C:54]=2[CH3:63])=[O:52])=[CH:47][C:43]=1[C:44](O)=[O:45].Cl.[CH3:65][O:66][C:67](=[O:70])[CH2:68][NH2:69].C(=O)([O-])O.[Na+]>CN1C(=O)CCC1>[NH2:41][C:42]1[CH:50]=[CH:49][C:48]([C:51]([C:53]2[N:61]3[C:56]([CH:57]=[CH:58][CH:59]=[CH:60]3)=[C:55]([Br:62])[C:54]=2[CH3:63])=[O:52])=[CH:47][C:43]=1[C:44]([NH:69][CH2:68][C:67]([O:66][CH3:65])=[O:70])=[O:45]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (7.34 mL; 52.3 mmol) and PyBOP (9.97 g; 19.2 mmol) are added to a solution of 2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoic acid (6.5 g; 17.4 mmol) in 58 mL of NMP at 0° C. under nitrogen. After 30 min of stirring at 0° C., glycine methyl ester hydrochloride (2.4 g; 19.2 mmol) is added. After 1 h of stirring at ambient temperature, the reaction medium is run into a saturated aqueous solution of sodium hydrogen carbonate. The yellow precipitate formed is filtered off and dried under vacuum to give 6.45 g (83%) of a yellow powder.

Workup

stirringAfter 1 h of stirring at ambient temperature
customThe yellow precipitate formed
filtrationis filtered off
customdried under vacuum

Sources & evidence

ORD record: ord-5a873fbbe2f348bc8d4d3c7c15e92bcc
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206177B2

Reaction notes

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