N-Hydroxysuccinimide → 843666-31-9

HRID 1632004Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:29])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:31]1[C:35](=[O:36])[CH2:34][CH2:33][C:32]1=[O:37]>CN1C(=O)CCC1>[O:37]=[C:32]1[CH2:33][CH2:34][C:35](=[O:36])[N:31]1[O:27][C:26](=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][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:29]

Participants

Conditions

Temperature: 60 °C

Procedure

1,18-octadecanedioic acid mono benzyl ester (120 g, 0.3 mol), N-hydroxysuccinimide (41 g, 0.36 mol) and N,N-dicyclohexylcarbodiimide (74 g, 0.36 mol) were dissolved in NMP (1200 ml) and heated to 60° C. for 2.5 hr. The reaction mixture was cooled to 25° C. and the precipitate was removed by filtration and washed with water (4.7 L). The crude precipitate was recystallised from 2-propanol (1250 ml), affording benzyl 18-[(2,5-dioxo-1-pyrrolidinyl)oxy]-18-oxooctadecanoate. Yield 138 g (92%).

Workup

temperatureThe reaction mixture was cooled to 25° C.
customthe precipitate was removed by filtration
washwashed with water (4.7 L)

Sources & evidence

ORD record: ord-74d5a577ea3141a69aca640faf963c45
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791236B2

Reaction notes

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