Acetaldehyde → HCID 67929082, compound

HRID 344786Notes

Reaction equation

HRID 344786 reaction equation
C(OC(N[CH:9]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[N:12]2[C:18](=[O:20])[CH2:19][C@H:11]2[S:10]1)=O)(C)(C)C.[CH3:21][CH2:22][N:23]([CH2:26]C)CC.[BH3-]C#[N:30].[Na+].C(=O)C>CO>[NH2:30][CH:19]1[C:18](=[O:20])[N:12]2[C:13]([C:15]([OH:17])=[O:16])=[C:14]([CH2:26][NH:23][CH2:22][CH3:21])[CH2:9][S:10][C@H:11]12

Participants

6

Reactant 4

HCID 177Acetaldehyde2×HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 67860817HCID 67860817, compound

Product 1

HCID 67929082HCID 67929082, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Aminomethyl-7-(t-butoxycarbonylaminoceph-3-em-4-carboxylic acid (987 mg at approximately 71% purity, equivalent to 700 mgs pure material) was added to a rapidly stirred solution of Et3N (215 mg, 0.294 ml) at ambient temperature: it did not dissolve completely. The mixture was stirred for 30 minutes, then NaCNBH3 (132 mg) was added, followed by acetaldehyde (0.119 ml, 93.7 mg) as a solution in methanol, over 40 minutes by infusion pump. The mixture was stirred for 1 hour at ambient temperature after which HPLC showed much starting material still remaining. A further 0.018 ml of acetaldehyde was added in one portion over about 20 seconds. HPLC after a further 30 minutes showed less starting material present. The mixture was evaporated to a foam, then dissolved in 50 ml water adjusted to pH 2-3 with acetic acid, and purified by medium pressure chromatography on HP-20 ss column using gradient elution with water up to 25% v/v acetonitrile. The product eluted at 13-15% acetonitrile.

Workup

  1. dissolutionit did not dissolve completely
  2. stirringThe mixture was stirred for 1 hour at ambient temperature after which HPLC
  3. waitHPLC after a further 30 minutes showed less starting
  4. customThe mixture was evaporated to a foam
  5. dissolutiondissolved in 50 ml water
  6. custompurified by medium pressure chromatography on HP-20 ss column
  7. washelution with water up to 25% v/v acetonitrile
  8. washThe product eluted at 13-15% acetonitrile

Sources & evidence

ORD record
ord-2a80cc057d624a6c9bdea98fabe28e7d
Source dataset
uspto-grants-1991_10
Patent number
US05053500

Reaction notes

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