N-Hydroxyphthalimide → HCID 22946318, compound

HRID 1698855Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([N:15]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:16][CH:17]=[CH2:18])=[O:14])[CH:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:7]=1.O[N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[O:35]=[C:26]1[C:27]2[C:28](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:30])[N:25]1[O:12][CH2:11][CH2:10][CH2:9][O:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([C:13]([N:15]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:16][CH:17]=[CH2:18])=[O:14])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of alcohol 17 (8.8 g, 26 mmol), tetrahydrofuran (100 mL), N-hydroxyphthalimide (3.8 g, 23 mmol) and triphenylphosphine (5.2 g, 20 mmol) was stirred at 0° C. for 5 min. To the mixture was added DEAD (3.4 mL. 20 mmol) dropwise. The reaction mixture was then allowed to warm to ambient temperature and stirred for 12 h prior to concentration in vacuo. The residue was purified by chromatography to provide phthalimide 18 (3.7 g) contaminated with Mitsunobu by-products. This material was used directly in subsequent experiments. 1H NMR (300 MHz, CDCl3) δ 7.78-7.85 (m, 2H), 7.73-7.77 (m, 2H), 6.94 (t, 2H), 6.38 (d, 1H), 5.95 (bs, 1H), 5.18 (d, 2H), 4.40 (t, 2H), 3.8-4.4 (m, 4H), 2.20-2.28 (m, 2H), 1.4-1.9 (m, 1H). Mass spectrum (CI) calcd. for C26H27N2O5Cl: 483 (M+H). Found: 483.

Workup

temperatureto warm to ambient temperature
stirringstirred for 12 h
concentrationto concentration in vacuo
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-686daa37767141a1acd6c4c40d7261a3
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06344466B2

Reaction notes

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