Acetaldehyde → HCID 131718396, compound

HRID 1464443Notes

Reaction equation

HRID 1464443 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][C:8]([NH:10][NH:11][C:12]([N:14]1[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[O:17][C:16]2[CH:25]=[CH:26][C:27]([NH2:29])=[CH:28][C:15]1=2)=[O:13])=[O:9])(=[O:5])=[O:4])[CH3:2].[CH:30](=O)[CH3:31].C([BH3-])#N.[Na+].O.[C:38](#N)[CH3:39]>C(O)(=O)C>[CH2:1]([S:3]([CH2:6][CH2:7][C:8]([NH:10][NH:11][C:12]([N:14]1[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[O:17][C:16]2[CH:25]=[CH:26][C:27]([N:29]([CH2:30][CH3:31])[CH2:38][CH3:39])=[CH:28][C:15]1=2)=[O:13])=[O:9])(=[O:5])=[O:4])[CH3:2]

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 962WaterHCID 6342AcetonitrileHCID 5003444Sodium cyanoborohydrideHCID 15293134HCID 15293134, compound

Product 1

HCID 131718396HCID 131718396, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of the title compound of Example 13 (2.0 g), acetaldehyde (3.0 mL), sodium cyanoborohydride (0.904 g), and water (2.6 mL) in acetonitrile (20 mL) was added glacial acetic acid (0.5 mL) over a period of 6 minutes. The reaction was stirred for 2.5 hours at ambient temperature, and then glacial acetic acid was added (0.5 mL), and the reaction was stirred for an additional 30 minutes. The resulting mixture was evaporated under vacuum, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The layers were separated, and the aqueous layer was extracted once more with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over magnesium sulfate, and evaporated under vacuum to a clear, greenish oil. The oil was chromatographed four times:twice through silica gel 60 using 97:3 ethyl acetate:ethanol; next through silica gel 60 using 3:1 chloroform:tetrahydrofuran; and finally through reverse phase silica gel (C18) using 80:20:1 acetonitrile:water:ammonium hydroxide. The product from the last column was co-evaporated three times with ethanol to azeotrope water from the product and dried under vacuum at room temperature to yield the title compound as a white solid containing 1.86% water. HPLC: 99.53% pure.

Workup

  1. stirringthe reaction was stirred for an additional 30 minutes
  2. customThe resulting mixture was evaporated under vacuum
  3. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted once more with ethyl acetate
  6. washThe combined ethyl acetate extracts were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under vacuum to a clear, greenish oil
  9. customThe oil was chromatographed four times
  10. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-cc2addb763b24e89ac288c0543b482f5
Source dataset
uspto-grants-1994_04
Patent number
US05304644

Reaction notes

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