2-Azetidinone → HCID 44624303, compound

HRID 420280Notes

Reaction equation

[NH2:1][C:2]1[C:31](I)=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)C(=O)[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:33].[NH:34]1[CH2:37][CH2:36][C:35]1=[O:38]>>[NH2:1][C:2]1[C:3]([F:33])=[CH:4][C:5]([CH2:6][C@H:7]2[C@H:15]([OH:14])[C@@H:11]([NH:12][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:25])[CH3:26])[CH:19]=3)[CH2:10][S:9](=[O:28])(=[O:29])[CH2:8]2)=[CH:30][C:31]=1[N:34]1[CH2:37][CH2:36][C:35]1=[O:38]

Participants

Reactant 2

HCID 1367212-Azetidinone

HCID 57386048HCID 57386048, compound

Product 1

HCID 44624303HCID 44624303, compound

Procedure

The title compound was prepared in analogous manner as described for example 4 from (3aR*,7S*,7aS*)-7-(4-amino-3-fluoro-5-iodo-benzyl)-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexa-hydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (example 1k) and azetidin-2-one: HPLC RtC=2.99 min; ESIMS [M+H]+=504; NMR (400 MHz, CDCl3+0.5% D2O): δ 7.65 (m, 2H), 7.56 (t, 1H), 7.47 (m, 3H), 6.30 (m, 2H), 4.20 (q, 2H), 3.80 (m, 2H), 3.59 (m, 2H), 3.35, (m, 2H), 3.18 (m, 2H), 2.95 (m, 1H), 2.85 (m, 1H), 2.75 (m, 2H), 1.30 (s, 9H).

Workup

customHPLC RtC=2.99 min

Sources & evidence

ORD record: ord-a356a47e20d847a88b782024b8a627fd
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093406B2

Reaction notes

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