Methyl bromoacetate → HCID 12914983, compound

HRID 1603672Notes

Reaction equation

[C:1]1([S:7][CH:8]2[NH:11][C:10](=[O:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16]>>[C:1]1([S:7][CH:8]2[N:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:10](=[O:12])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 60984Methyl bromoacetate

HCID 18206331898-69-8

Product 1

HCID 12914983HCID 12914983, compoundYield 53.5%

Procedure

Treatment of 4-phenylthioazetidin-2-one (Iwata-Reuyl et. al., J. Nat. Prod., 1993, 56(8), 1373) (8 g) with methyl bromoacetate (7.5 g) under the conditions described for Example 1b gave the title compound as a colourless oil (6 g, 53% yield). 1H NMR δ (CDCl3) 2.87 (1H, dd, H3a), 3.42 (1H, dd, H3b), 3.70 (3H, s, CH3), 3.75, 4.29 (each 1H, d, NCH2), 5.22, (1H, dd, H4), 7.26-7.46 (5H, m, Ph-H).

Sources & evidence

ORD record: ord-441f47d6b8ff4f7fa4cc5eec1eb286c6
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990102

Reaction notes

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