Water → HCID 68077581, compound

HRID 1488253Notes

Reaction equation

CC1C=CC(S([O-])(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH3+:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:28]([O-:31])([O-:30])=O.[K+].[K+].[O:34]=[C:35]1[O:40][C:39](=[O:41])[CH2:38][N:37]([CH2:42]CC(O)=O)[CH2:36]1.O>CN(C=O)C>[CH2:12]([O:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:39](=[O:41])[CH2:38][N:37]([CH2:36][C:35]([OH:40])=[O:34])[CH2:42][C:28]([OH:31])=[O:30])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-(benzyloxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate (2.0 g, 5.08 mmol) in DMF (10 mL) at 0° C. was added K2CO3 (738 mg, 5.34 mmol). After stirring at 0° C. for 2 hr, the supernant of the reaction mixture was added to a solution of 3-(2,6-dioxomorpholin-4-yl)propanoic acid (1.10 g, 6.35 mmol) in DMF (10 mL) at 0° C. After stirring at 0° C. for 30 min, the reaction mixture was allowed to stir at rt for 1 hr and then cooled down to 0° C. followed by the addition of water (10 mL). The resulting mixture was concentrated and the residue was suspended in water (10 mL). After stirring at 0° C. for 16 hr, the solid was collected through filtration and dried to yield the title compound. 1H NMR (CD3OD) δ 7.36-7.30 (m, 5H), 5.11 (s, 2H), 3.56 (s, 4H), 3.43 (s, 2H), 3.23 (t, J=6.7, 2H), 2.39 (t, J=7.3, 2H), 1.68-1.62 (m, 2H), 1.57-1.51 (m, 2H), 1.40-1.35 (m, 2H).

Workup

stirringAfter stirring at 0° C. for 30 min
stirringto stir at rt for 1 hr
temperaturecooled down to 0° C.
concentrationThe resulting mixture was concentrated
stirringAfter stirring at 0° C. for 16 hr
filtrationthe solid was collected through filtration
customdried

Sources & evidence

ORD record: ord-f648ca3351af42cd903dde3efd9469ac
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09427475B2

Reaction notes

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