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1,2-Dichloroethane → benzyl 6-{bis[2-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]amino}-6-oxohexanoate

HRID 1488250
Notes
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Reaction equation

HRID 1488250 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([N:16]([CH2:21][C:22]([OH:24])=O)[CH2:17][C:18]([OH:20])=O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:26]([CH2:37][CH2:38][NH2:39])[C@@H:27]1[O:35][C@@H:34]([CH3:36])[C@@H:32]([OH:33])[C@@H:30]([OH:31])[C@@H:28]1[OH:29].[CH2:40](Cl)[CH2:41]Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C@@H:27]1([O:26][CH2:37][CH2:38][NH:39][C:22](=[O:24])[CH2:21][N:16]([CH2:17][C:18](=[O:20])[NH:39][CH2:38][CH2:37][O:26][C@@H:27]2[O:35][C@@H:40]([CH3:41])[C@@H:32]([OH:33])[C@@H:30]([OH:31])[C@@H:28]2[OH:29])[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:25])[O:35][C@@H:34]([CH3:36])[C@@H:32]([OH:33])[C@@H:30]([OH:31])[C@@H:28]1[OH:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 10954744(2R,3S,4R,5S,6S)-2-(2-Aminoethoxy)-6-methyltetrahydro-2H-pyran-3,4,5-triolHCID 1179960702,2'-{[6-(Benzyloxy)-6-oxohexanoyl]imino}diacetic acid

Product 1

HCID 117995876benzyl 6-{bis[2-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]amino}-6-oxohexanoate

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2,2′-{[6-(benzyloxy)-6-oxohexanoyl]imino}diacetic acid (800 mg, 2.277 mmol) in DMF (12 mL) at room temperature was added 2-aminoethyl α-L-fucopyranoside (1.132 g, 5.46 mmol), DMAP (834 mg, 6.83 mmol) and EDC (1.528 g, 7.97 mmol). After stirring at rt for 16 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on C18 reverse phase silica gel (120 g), eluting with 0-40% AcCN in water, to give the title compound. LC-MS Method A: m/e=730.26 [M+1]; Rt=1.42 min.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on C18 reverse phase silica gel (120 g)
  3. washeluting with 0-40% AcCN in water

Sources & evidence

ORD record
ord-3ff88908113a4ee9aed8e25a586426fb
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09427475B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes