Azetidine → HCID 58109604, compound

HRID 2037600Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)([CH2:16][CH2:17]O)[O:12][C:11]2=[O:26])[CH3:9])=[CH:4][CH:3]=1.[NH:27]1[CH2:30][CH2:29][CH2:28]1>>[N:27]1([CH2:17][CH2:16][C@@:13]2([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[O:12][C:11](=[O:26])[N:10]([C@H:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)[CH3:9])[CH2:15][CH2:14]2)[CH2:30][CH2:29][CH2:28]1

Participants

Reactant 2

HCID 10422Azetidine

HCID 58109626HCID 58109626, compound

Product 1

HCID 58109604HCID 58109604, compound

Procedure

The title compound was prepared from (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one and azetidine following procedures analogous to those described in Example 178. LC-MS Method 2 tR=1.15 min, m/z=463; 1H NMR (CDCl3) 1.43 (d, 4H), 2.05-2.27 (m, 7H), 2.56-2.74 (m, 2H), 2.86 (m, 1H), 3.20 (m, 1H), 3.50 (m, 1H), 3.71 (m, 1H), 4.17-4.39 (d, 2H), 5.52 (m, 1H), 6.80 (d, 2H), 6.95-7.02 (m, 2H), 7.13-7.24 (m, 4H).

Sources & evidence

ORD record: ord-39d8adf9a12c4aae99951ca7660a1934
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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