Water → (4'-Fluoro[1,1'-biphenyl]-4-yl)acetic acid

HRID 1907902Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)CN.C1CN([P+](ON2N=N[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN([CH:49]([CH3:51])C)C(C)C.[OH2:52].CN(C=[O:57])C>>[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:28]2[CH:29]=[CH:30][C:31]([CH2:51][C:49]([OH:57])=[O:52])=[CH:32][CH:33]=2)=[CH:4][CH:3]=1

Participants

Reactant 5

HCID 962Water

HCID 6228Dimethylformamide

HCID 668533-Fluorobenzylamine

HCID 81531Diisopropylethylamine

HCID 2724699PyBOP

Product 1

HCID 1393927(4'-Fluoro[1,1'-biphenyl]-4-yl)acetic acid

Procedure

3-fluorobenzylamine (0.14 ml, 1.1 mmole), PyBOP (0.57 gm, 1.1 mmole), and DIEA (0.36 ml, 2.2 mmole) was dissolved in DMF stirred overnight, the reaction mixture was then poured into water, solid was collected by filtration, re-crystallized using water-methanol. (0.22 gm, 76%); H1-NMR INOVA-500 (DMSO d6) δ 3.550(s, 2H), 4.303(d, J=6.5 Hz, 2H), 7.027-7.097(m, 3H), 7.197(m, 1H), 7.350(m, 1H), 7.389(d, J=8.0 Hz, 2H), 7.477-7.518(m, 3H), 7.657(d, J=8.0 Hz, 2H), 8.652(t, J=5.5 Hz, 1H). MS (m/z) 338.1 (M+H)+.

Workup

filtrationwas collected by filtration
customre-crystallized

Sources & evidence

ORD record: ord-3faef5dc38cd4b8bb929a49fe4aad5f3
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598169B2

Reaction notes

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