Diisopropylethylamine → HCID 117996333, compound

HRID 1488257Notes

Reaction equation

[C@@H:1]1([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:32])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][C@@H:27]([C:29]([OH:31])=[O:30])[NH2:28])=[O:21])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].O=C1CCC(=O)N1[O:40][C:41](=O)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49].CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:51]([O:50][C:48](=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][C:41]([NH:28][C@H:27]([C:29]([OH:31])=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23][NH:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][C:15]([NH:14][CH2:13][CH2:12][O:11][C@@H:1]1[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3])=[O:32])=[O:40])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of N6-[6-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)-6-oxohexanoyl]-L-lysine (310 mg, 0.669 mmol) in DMF (20 mL) at 0° C. was added benzyl 8-[(2,5-dioxopyrrolidin-1-yl)oxy]-8-oxooctanoate (242 mg, 0.669 mmol), followed by the addition of DIPEA (0.117 ml, 0.669 mmol). The reaction was warmed to 25° C. and stirred at this temp for 18 hr. The reaction mixture was concentrated, and the residue was purified by flash chromatography on C18 reverse phase silica gel, eluting with 0-30% CAN in water, to give the title compound. UPLC Method B: m/e=710.423 [M+1]; Rt=4.59 min.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by flash chromatography on C18 reverse phase silica gel
washeluting with 0-30% CAN in water

Sources & evidence

ORD record: ord-e1ebf73820a1493c93174fd8ee08fb43
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09427475B2

Reaction notes

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