Acetic Acid → HCID 117996061, compound

HRID 1488280Notes

Reaction equation

HRID 1488280 reaction equation
[C:1]([O:4][C@H:5]1[C@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@H:12]([CH3:23])[O:11][C@H:6]1[O:7][CH2:8][CH2:9][NH2:10])(=[O:3])[CH3:2].[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>C(Cl)Cl>[C:1]([O:4][C@H:5]1[C@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@H:12]([CH3:23])[O:11][C@H:6]1[O:7][CH2:8][CH2:9][NH:10][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 117996036HCID 117996036, compound

Product 1

HCID 117996061HCID 117996061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminoethyl 2,3,4-tri-O-acetyl-α-L-fucopyranoside (8.56 g, 25.7 mmol) in CH2Cl2 (100 mL) was added benzaldehyde (2.197 ml, 21.67 mmol), acetic acid (372 μL, 6.50 mmol) and NaCNBH3 (3.40 g, 54.2 mmol). After stirring at rt for 16 hr, the reaction mixture was concentrated and the residue was partitioned between EtOAc (50 mL) and sat. NaHCO3 (50 mL). The organic phase separated, washed with sat'd NaHCO3 (2×100 mL), brine (100 mL), dried over MgSO4, and concentrated. The residue was purified by flash chromatography on C18 reverse phase silica gel (130 g), eluting with 0-100% AcCN in water to give the title compound. UPLC Method B: m/e=424.2089 [M+1]; Rt=3.42 min.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc (50 mL) and sat. NaHCO3 (50 mL)
  3. customThe organic phase separated
  4. washwashed with sat'd NaHCO3 (2×100 mL), brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on C18 reverse phase silica gel (130 g)
  8. washeluting with 0-100% AcCN in water

Sources & evidence

ORD record
ord-a13fc0c809854125aa67b4c07a285b35
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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