Diisopropylethylamine → Benzyl (2,5-dioxopyrrolidin-1-yl) adipate

HRID 1488237Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CN(C(O[N:31]1[C:36](=[O:37])[CH2:35][CH2:34][C:32]1=[O:33])=[N+](C)C)C.CCN(C(C)C)C(C)C>CN(C=O)C>[O:33]=[C:32]1[CH2:34][CH2:35][C:36](=[O:37])[N:31]1[O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-(benzyloxy)-6-oxohexanoic acid (3.3 g, 13.97 mmol) in DMF (50 mL) at 0° C. was added TSTU (4.3 g, 14.28 mmol) and DIPEA (2.5 mL, 14.31 mmol). After stirring at 0° C. for 1 hour, the reaction mixture was partitioned between Et2O and water. The organic layer was separated and the aqueous layer was further extracted with ether (2×150 mL). The combined organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound. UPLC Method B: calculated for C17H19NO6 333.12, observed m/e: 334.10 [M+1]; Rt=3.75 min. 1H NMR (CDCl3) δ 7.40-7.30 (5H, m), 5.10 (2H, s), 2.80 (4H, s), 2.62-2.58 (2H, m), 2.41-2.37 (2H, m), 1.80-1.72 (4H, m).

Workup

customthe reaction mixture was partitioned between Et2O and water
customThe organic layer was separated
extractionthe aqueous layer was further extracted with ether (2×150 mL)
washThe combined organic phase was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-6928e0856ab446fe84dfaab3b7bc69bf
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09427475B2

Reaction notes

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