Peracetic Acid → 1-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl 2-methylpropanoate

HRID 898363Notes

Reaction equation

HRID 898363 reaction equation
[CH3:1][CH:2]([CH3:14])[C:3]([O:5][CH:6]([O:10][C:11](C)=S)[CH:7]([CH3:9])[CH3:8])=[O:4].[OH:15][N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22].C(OO)(=[O:25])C>ClCCl>[CH3:1][CH:2]([CH3:14])[C:3]([O:5][CH:6]([O:10][C:11]([O:15][N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22])=[O:25])[CH:7]([CH3:9])[CH3:8])=[O:4]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 80170N-HydroxysuccinimideHCID 866102712-Methyl-1-methylthiocarbonyloxypropyl 2-methylpropanoate

Product 1

HCID 448146361-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl 2-methylpropanoateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the above general procedure, 2-methyl-1-(methylthiocarbonyloxy)-propyl 2-methylpropanoate (2.34 g, 10.0 mmol) and N-hydroxysuccinimide (5.76 g, 50 mmol) were reacted in dichloromethane (30 mL) with peracetic acid (32 wt. %, 8.17 mL). After aqueous workup, isolation and removal of residual solvents in vacuo, the crude product 3 (2.12 g, 70%) was obtained as a pale yellow oil. The material was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ=1.04 (d, J=7.2 Hz, 6H), 1.21 (d, J=6.8 Hz, 3H), 1.22 (d, J=6.8 Hz, 3H), 2.15-2.21 (m, 1H), 2.63 (hept., J=7.2 Hz, 1H), 2.84 (s, 4H), 6.59 (d, J=5.2 Hz, 1H). MS (ESI) m/z 324.10 (M+Na)+.

Workup

  1. customAfter aqueous workup, isolation and removal of residual solvents in vacuo

Sources & evidence

ORD record
ord-70619272f2174deeaf80445d81dec451
Source dataset
uspto-grants-2008_04
Patent number
US07351740B2

Reaction notes

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