Peracetic Acid → HCID 86610269, compound

HRID 734905Notes

Reaction equation

HRID 734905 reaction equation
[CH3:1][CH:2]([CH3:14])[C:3]([O:5][CH:6]([O:9][C:10](CC)=S)[CH2:7][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>[CH3:14][CH:2]([CH3:1])[C:3]([O:5][CH:6]([O:9][C:10]([O:15][N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22])=[O:25])[CH2:7][CH3:8])=[O:4]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 80170N-HydroxysuccinimideHCID 86610270HCID 86610270, compound

Product 1

HCID 86610269HCID 86610269, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the above general procedure, 1-(ethylthiocarbonyloxy)-propyl 2-methylpropanoate (2.3 g, 9.82 mmol) and N-hydroxysuccinimide (4.6 g, 40 mmol) were reacted in dichloromethane (20 mL) with peracetic acid (32 wt. %, 6.13 mL). After aqueous workup, isolation and removal of residual solvents in vacuo, the crude product 2 (1.76 g, 61%) was obtained as a yellow oil. The material was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ=1.02 (t, J=7.6 Hz, 3H), 1.20 (d, J=6.8 Hz, 3H), 1.21 (d, J=7.2 Hz, 3H), 1.88-2.00 (m, 2H), 2.61 (hept., J=7.2 Hz, 1H), 2.84 (s, 4H), 6.71 (t, J=5.2 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-b277984ac23143beafab9ff6547dec05
Source dataset
uspto-grants-2009_09
Patent number
US07592369B2

Reaction notes

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