3-Fluorophenylacetic acid → HCID 10095835, compound

HRID 2267672Notes

Reaction equation

HRID 2267672 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C@H:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:3]1[NH:19][C:20](=[O:33])[C@H:21]([CH3:32])[NH:22][C:23](=[O:31])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[F:34]C1C=C(CC(O)=O)C=CC=1>>[F:34][C:29]1[CH:30]=[C:25]([CH2:24][C:23]([NH:22][C@H:21]([C:20]([NH:19][C@@H:3]2[C:2](=[O:1])[NH:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[O:5][C@@H:4]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:33])[CH3:32])=[O:31])[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 676173-Fluorophenylacetic acidHCID 10252847HCID 10252847, compound

Product 1

HCID 10095835HCID 10095835, compound

Procedure

A method similar to the one described for (113) was used except that 3-fluorophenylacetic acid (77 mg) was used in place of phenylacetic acid to afford the title, compound as a 1:1 mixture with the (2S,3R) diastereomer (140 mg), white solid, m.p. 130-140° C. 1H NMR (300 MHz, CDCl3) δ 0.97 (d, 1.5H, J=5 Hz), 1.27 (d, 1.5H, J=5 Hz), 3.45 (two peaks, 2H), 4.52 (m, 0.5H), 4.67 (m, 0.5H), 4.91 (t, 1H, J=6 Hz), 5.12 (t, 1H, J=6 Hz), 5.79 (dd, 1H, J=7 Hz, J=10 Hz), 6.15 (d, 0.5H, J=8 Hz), 6.28 (d, 0.5 Hz, J=8 Hz), 6.63 (d, 0.5h, J=6 Hz), 6.70 (d, 0.5H, J=7 Hz), 6.86-7.70 (m, 13H), 7.96 (s, 1H). MS APCI, m/z=484 (M+Na). LC/MS: 2.09 min.

Workup

  1. customto afford the title, compound as a 1:1 mixture with the (2S,3R) diastereomer (140 mg), white solid, m.p. 130-140° C
  2. custom2.09 min.

Sources & evidence

ORD record
ord-9c53adb16fe849a4861aa519c04b43c7
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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