2,2-Dimethyl-1,3-dioxane-4,6-dione → Tert-butyl (4r)-4-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)carbonyl]-1,3-thiazolidine-3-carboxylate

HRID 458444Notes

Reaction equation

HRID 458444 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=O)[CH2:11][S:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1([CH3:25])[O:24][C:22](=[O:23])[CH2:21][C:19](=[O:20])[O:18]1>>[CH3:16][C:17]1([CH3:25])[O:24][C:22](=[O:23])[CH:21]([C:13]([C@@H:12]2[CH2:11][S:10][CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15])[C:19](=[O:20])[O:18]1

Participants

3

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 688405(4R)-3-[(tert-butoxy)carbonyl]-1,3-thiazolidine-4-carboxylic acid

Product 1

HCID 90819551Tert-butyl (4r)-4-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)carbonyl]-1,3-thiazolidine-3-carboxylateYield 89%

Procedure

A was prepared from (4R)-3-(tert-butoxycarbonyl)-1,3-thiazolidine-4-carboxylic acid (5.30 g, 22.7 mmol) and Meldrum's acid according to the previously described procedure used for Example 1C, giving the title compound as yellow solid (7.31 g, 89%). LCMS m/z 358 (M−H). 1H NMR (300 MHz, CDCl3, mixture of rotamers) δ 5.88 (m, 1H), 4.80–4.51 (m, 3H), 369 (m, 1H), 3.05 (m, 1H), 2.0–1.8 (m, 3H), 1.8–1.7 (m, 6H), 1.44 (s, 5H), 1.38 (s, 4H) ppm.

Sources & evidence

ORD record
ord-4b79f405a28a495fa502027334fb847e
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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