1,2-Dichloroethane → Tert-butyl[3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-methyl-3-oxopropyl]carbamate

HRID 589995Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH3:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]1([CH3:24])[O:21][C:20](=[O:22])[CH2:19][C:18](=[O:23])[O:17]1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([CH3:14])[C:11]([CH:19]1[C:20](=[O:22])[O:21][C:16]([CH3:24])([CH3:15])[O:17][C:18]1=[O:23])=[O:13])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

The 3-[(tert-butoxycarbonyl)amino]-2-methylpropanoic acid (3.0 g, 14.76 mmol) was dissolved in CH2Cl2 (73.8 ml), cooled to 0° C. and treated with 2,2-dimethyl-1,3-dioxane-4,6-dione (2.55 g, 17.71 mmol) and DMAP (2.71 g, 22.14 mmol) and EDC (3.40 g, 17.71 mmol) and allowed to stir at room temperature for 18 hrs. The reaction mixture was diluted with CH2Cl2, washed with 5% KHSO4 (×3), dried (Na2SO4), filtered and evaporated in vacuo to give the title compound: 1H NMR (400 MHz, CDCl3) δ 4.78 (bs, 1H), 4.23 (bs, 1H), 3.42 (m, 2H), 1.75 (s, 6H), 1.41 (s, 9H), 1.23 (d, J=6.8 Hz, 3H).

Workup

washwashed with 5% KHSO4 (×3)
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-ea0ee8e737174ad7b37e83eb940f70a0
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233977B2

Reaction notes

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