Acetaldehyde → HCID 88485753, compound

HRID 728594Notes

Reaction equation

HRID 728594 reaction equation
[NH2:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:13]([NH:14][C:15](=[O:31])/[C:16](/[C:25]3[N:26]=[C:27]([NH2:30])[S:28][CH:29]=3)=[N:17]\[O:18][CH:19]([C:22]([OH:24])=[O:23])[CH2:20][CH3:21])[C:12](=[O:32])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10].C([BH3-])#N.[Na+].[CH:37](=O)[CH3:38]>C([O-])(=O)C.[Na+].O>[NH2:30][C:27]1[S:28][CH:29]=[C:25](/[C:16](=[N:17]/[O:18][CH:19]([C:22]([OH:24])=[O:23])[CH2:20][CH3:21])/[C:15]([NH:14][CH:13]2[C:12](=[O:32])[N:7]3[C:8]([C:9]([OH:11])=[O:10])=[C:3]([CH2:2][NH:1][CH2:37][CH3:38])[CH2:4][S:5][C@H:6]23)=[O:31])[N:26]=1

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 88485746HCID 88485746, compound

Product 1

HCID 88485753HCID 88485753, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 517045Sodium AcetateSolvent

Procedure

The cephalosporin starting material may be prepared as follows: To a stirred solution of 3-aminomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-1-carboxypropoxyimino)acetamido]ceph-3-em-4-carboxylic acid (more polar isomer, 2.6 g) in 2.5% (w/v) pH 5.5 sodium acetate buffer (50 ml) was added sodium cyanoborohydride (0.34 g), followed by acetaldehyde (0.3 ml) in water (5 ml) over 40 minutes. The reaction mixture was then concentrated, diluted to 50 ml with water, and the pH adjusted to 3.5 with HOAc. Careful chromatography on Diaion HP20SS, eluting with H2O/CH3CN, (92.5:7.5) gave 7-[2-(2-aminothiazol-4-yl)-2-((Z)-1-carboxypropoxyimino)acetamido]-3-ethylaminomethylceph-3-em-4-carboxylic acid, having the following n.m.r. spectrum in solvent A: 0.96 (t, 3H); 1.18 (t, 3H); 1.81 (quintet, 2H); 2.94 (q, 2H); 3.38 (d, 1H); 3.42 (d, 1H); 3.61 (d, 1H); 3.78 (d, 1H); 4.46 (t, 1H); 5.03 (d, 1H); 5.76 (d, 1H); 6.88 (s, 1H). Retention time 4.2 minutes on a reversed phase Partisil PXS 10/25 ODS-2 column, using MeOH/H2O/HOAc, 30:70:1, v/v/v, as eluant.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted to 50 ml with water
  3. washCareful chromatography on Diaion HP20SS, eluting with H2O/CH3CN, (92.5:7.5)

Sources & evidence

ORD record
ord-5e6a8ade5b1c4860825a225bf2b568d6
Source dataset
uspto-grants-1991_09
Patent number
US05049558

Reaction notes

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