HCID 59627212, compound → HCID 68777840, compound

HRID 1523250Notes

Reaction equation

C([C@@]1(C2C=CC(F)=CC=2)CCN([C@H](C2C=CC(C3C=CC(F)=CC=3)=CC=2)C)C(=O)N1)C=C.[OH:33][CH:34]([CH2:65][OH:66])[CH2:35][C@@:36]1([C:58]2[CH:63]=[CH:62][C:61]([F:64])=[CH:60][CH:59]=2)[CH2:41][CH2:40][N:39]([C@H:42]([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=3)=[CH:46][CH:45]=2)[CH3:43])[C:38](=[O:57])[NH:37]1>>[OH:33][CH:34]([CH2:65][OH:66])[CH2:35][C:36]1([C:58]2[CH:59]=[CH:60][C:61]([F:64])=[CH:62][CH:63]=2)[CH2:41][CH2:40][N:39]([C@H:42]([C:44]2[CH:45]=[CH:46][C:47]([C:50]3[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=3)=[CH:48][CH:49]=2)[CH3:43])[C:38](=[O:57])[NH:37]1

Participants

Reactant 2

HCID 59627212HCID 59627212, compound

HCID 59627215HCID 59627215, compound

Product 1

HCID 68777840HCID 68777840, compound

Procedure

Treatment of (S)-4-allyl-1-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-4-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one with AD-mix 13 following a procedure analogous to that described in Example 8 afforded (4R)-4-(2,3-dihydroxypropyl)-1-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-4-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one isomers 3 and 4 which were separated by prep HPLC. Isomer 3: LC-MS Method 1 tR=1.337 min, m/z=467.2; 1H NMR (CDCl3) 1.31 (d, 3H), 1.84-2.03 (m, 5H), 2.52 (m, 1H), 2.68 (m, 1H), 3.33 (m, 1H), 3.42 (m, 1H), 3.79 (s, 1H), 5.66 (m, 1H), 6.79 (s, 1H), 7.03 (m, 4H), 7.29 (m, 4H), 7.44 (m, 4H). Isomer 4: LC-MS Method 1 tR=1.382 min, m/z=467.2; 1H NMR (CDCl3) 1.33 (d, 3H), 1.76-1.88 (m, 2H), 2.04 (m, 2H), 2.57 (m, 1H), 2.71 (m, 1H), 3.52 (m, 3H), 5.76 (m, 1H), 7.12 (m, 4H), 7.33 (m, 4H), 7.52 (m, 4H), 7.61 (s, 1H).

Workup

customwere separated by prep HPLC

Sources & evidence

ORD record: ord-9d360240b8cb4071ac16bb4a81e8c1b4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079861B2

Reaction notes

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