Azetidine → HCID 58109138, compound

HRID 2037652Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C@@:19]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)([CH2:22][CH2:23]O)[O:18][C:17]3=[O:32])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH:33]1[CH2:36][CH2:35][CH2:34]1>>[N:33]1([CH2:23][CH2:22][C@@:19]2([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[O:18][C:17](=[O:32])[N:16]([C@H:14]([C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:13][CH:12]=3)[CH3:15])[CH2:21][CH2:20]2)[CH2:36][CH2:35][CH2:34]1

Participants

Reactant 2

HCID 10422Azetidine

HCID 53473233HCID 53473233, compound

Product 1

HCID 58109138HCID 58109138, compound

Procedure

The title compound was prepared from (S)-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one following procedures analogous to those described in Example 178 using azetidine in Step 2. LC-MS Method 2 tR=1.193 min, m/z=477.2; 1H NMR (CD3OD) 1.57 (d, 3H), 2.16 (m, 2H), 2.26 (m, 2H), 2.48 (m, 1H), 2.50 (m, 2H), 3.01 (m, 1H), 3.11 (m, 1H), 3.25 (m, 1H), 3.40 (m, 2H), 4.20 (m, 2H), 5.59 (m, 1H), 7.08 (d, 2H), 7.14 (m, 4H), 7.33 (m, 2H), 7.37 (m, 2H), 7.54 (m, 2H).

Sources & evidence

ORD record: ord-49935207b01748e9872010aa7fa55d31
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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