Acetyl chloride → 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-methoxycarbonylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 2413427Notes

Reaction equation

HRID 2413427 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]2[CH2:14][S:13][CH:12]3[N:9]([C:10](=[O:23])[CH:11]3[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]=2[C:24]([O:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[CH:5][N:6]=1.C(Cl)(=O)C.Cl[C:45]([O:47][CH3:48])=[O:46]>>[CH:27]([O:26][C:24]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:7]=1[C:4]1[S:3][C:2]([NH:1][C:45]([O:47][CH3:48])=[O:46])=[N:6][CH:5]=1)[CH:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]2=[O:23])=[O:25])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 6586Methyl chloroformateHCID 131759453-(2-Aminothiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 204304182-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-methoxycarbonylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Procedure

3-(2-Amino-thiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene (1.13 g) is treated in accordance with the working method described in Example 1 (B), the acetyl chloride being replaced by methyl chloroformate (0.19 cc). The crude product obtained is chromatographed on a column (height: 30 cm, diameter: 3 cm) of silica gel (0.04-0.06 mm), elution being carried out under a pressure of 0.4 bar (40 kPa) with a 40:60 (by volume) mixture of cyclohexane and ethyl acetate; 50 cc fractions are collected and are analysed by chromatography on a thin layer of silica gel (eluant: a 40:60 (by volume) mixture of cyclohexane and ethyl acetate). The fractions containing the pure expected product (Rf=0.3) are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-methoxycarbonylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.73 g) is obtained in the form of a yellow froth.

Workup

  1. customThe crude product obtained
  2. customis chromatographed on a column (height: 30 cm, diameter: 3 cm) of silica gel (0.04-0.06 mm), elution
  3. additionbeing carried out under a pressure of 0.4 bar (40 kPa) with a 40:60 (by volume) mixture of cyclohexane and ethyl acetate
  4. custom50 cc fractions are collected
  5. additiona 40:60 (by volume) mixture of cyclohexane and ethyl acetate)
  6. additionThe fractions containing the pure expected product (Rf=0.3)
  7. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C

Sources & evidence

ORD record
ord-30a6c358e18144d28e2369035d37f2a1
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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