Dipropanolamine → Benzyl 6-(bis(3-hydroxypropyl)amino)-6-oxohexanoate

HRID 1488308Notes

Reaction equation

HRID 1488308 reaction equation
[NH:1]([CH2:6][CH2:7][CH2:8][OH:9])[CH2:2][CH2:3][CH2:4][OH:5].[C:10]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:25])[CH2:11][CH2:12][CH2:13][CH2:14][C:15](ON1C(=O)CCC1=O)=[O:16]>CN(C=O)C>[OH:5][CH2:4][CH2:3][CH2:2][N:1]([CH2:6][CH2:7][CH2:8][OH:9])[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][C:10]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]

Participants

4

Reactant 2

HCID 106986DipropanolamineHCID 117996037Benzyl (2,5-dioxopyrrolidin-1-yl) adipate

Product 1

HCID 117996143Benzyl 6-(bis(3-hydroxypropyl)amino)-6-oxohexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,3′-azanediylbis(propan-1-ol) (1000 mg, 7.51 mmol, 1.0 eq) was in DMF (10 ml), was added benzyl (2,5-dioxopyrrolidin-1-yl) adipate (2503 mg, 7.51 mmol, 1.0 eq) followed by TEA (1.046 ml, 7.51 mmol, 1.0 eq). The reaction was stirred at 25 deg for 18 hr. UPLC indicated formation of desired product. DMF was removed under reduced pressure. The crude was purified by C18 Reverse phase chromatograph (eluted with 0-40% ACN/water in 16 CV). Fractions containing desired product were combined and concentrated to give the titled compound as colorless oil (1.55 g, 4.41 mmol, 58.7%). UPLC Method B: m/e=352.2171 [M+1]; Rt=3.47 min. 1H NMR (CDCl3, 500 MHz) δ 7.3-7.5 (m, 5H), 5.15 (m, 2H), 3.65 (m, 2H), 3.40 (m, 5H), 2.66 (s, 3H), 2.45 (m, 3H), 2.29 (s, 1H), 1.84 (s, 1H), 1.70 (m, 7H).

Sources & evidence

ORD record
ord-e161395c62e94ffa83eddb771612d401
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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