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

HRID 874473Notes

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-0f69786503284a4a8afe30c7fe3a77cd
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980890B2

Reaction notes

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