Benzyl chloroformate → HCID 131716886, compound

HRID 2050669Notes

Reaction equation

HRID 2050669 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:12]([O:19][C@H:20]1[C@H:26]2[CH2:27][CH2:28][NH:29][C@@H:21]1[CH:22]([O:25]2)[O:23][CH3:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>CCOCC>[CH2:12]([O:19][C@H:20]1[C@H:26]2[CH2:27][CH2:28][N:29]([C:2]([O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:3])[C@@H:21]1[CH:22]([O:25]2)[O:23][CH3:24])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 67923335HCID 67923335, compound2×

Product 1

HCID 131716886HCID 131716886, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Benzyl chloroformate (1.30 ml, 9.17 mmol) was added to a solution of methyl 3-O-benzyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexofuranoside epimers (22αβ) (α:β 1:2) (1.52 g, 6.11 mmol), in a stirred 3:2 mixture of ether and saturated sodium bicarbonate (60 ml). After 18 hours the ether layer was removed and the aqueous phase extracted further with ether (3×50 ml). The combined ether extracts were dried, filtered and evaporated. Purification by flash chromatography afforded both the methyl 3-O-Benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexofuranoside anomers as clear oils.

Workup

  1. customAfter 18 hours the ether layer was removed
  2. extractionthe aqueous phase extracted further with ether (3×50 ml)
  3. dry with materialThe combined ether extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-9cf5ae5a60dc43c7a5df374842e19dac
Source dataset
uspto-grants-1991_05
Patent number
US05013842

Reaction notes

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