Diethyl Ether → N,N-bis[2-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]-6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexanamide

HRID 1488252Notes

Reaction equation

[C@@H:1]1([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:44])[CH2:16][N:17]([CH2:27][C:28](=[O:43])[NH:29][CH2:30][CH2:31][O:32][C@@H:33]2[O:41][C@@H:40]([CH3:42])[C@@H:38]([OH:39])[C@@H:36]([OH:37])[C@@H:34]2[OH:35])[C:18](=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].[B-](F)(F)(F)F.CN(C(O[N:58]1[C:63](=[O:64])[CH2:62][CH2:61][C:59]1=[O:60])=[N+](C)C)C.CCN(C(C)C)C(C)C.CCOCC>CN(C=O)C>[C@@H:1]1([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:44])[CH2:16][N:17]([CH2:27][C:28](=[O:43])[NH:29][CH2:30][CH2:31][O:32][C@@H:33]2[O:41][C@@H:40]([CH3:42])[C@@H:38]([OH:39])[C@@H:36]([OH:37])[C@@H:34]2[OH:35])[C:18](=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][N:58]2[C:63](=[O:64])[CH2:62][CH2:61][C:59]2=[O:60])=[O:24])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 6-{bis[2-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]amino}-6-oxohexanoic acid (160 mg, 0.250 mmol) in DMF (3.0 mL) at 0° C. was added a solution of TSTU (94 mg, 0.313 mmol) in DMF (2 mL) and, 5 min later, DIPEA (53 μL, 0.300 mmol). After stirring for 1.5 h at 0° C., the mixture was added dropwise to Et2O (30 mL) in a centrifuge tube. After centrifuged for 30 min at 3500 rpm, the supernatant was decanted and the solid residue was dissolved in H2O, which was freeze-dried to give the title product. UPLC Method B: m/e=737 [M+1]; Rt=2.19 min.

Workup

waitAfter centrifuged for 30 min at 3500 rpm
customthe supernatant was decanted
dissolutionthe solid residue was dissolved in H2O
customwhich was freeze-dried

Sources & evidence

ORD record: ord-2d3dcdce863142c8bb0396adf2ec3878
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09427475B2

Reaction notes

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