Methanesulfonic Acid → HCID 13175960, compound

HRID 370599Notes

Reaction equation

HRID 370599 reaction equation
[NH:1]([C:8]1[S:9][C:10]([C:13]2[CH2:20][S:19][CH:18]3[N:15]([C:16](=[O:29])[CH:17]3[NH:21][C:22](OC(C)(C)C)=[O:23])[C:14]=2[C:30]([O:32][CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O)(=O)=O.[S:51]1[CH:55]=[CH:54][CH:53]=[C:52]1[CH2:56]C(Cl)=O.C(N(CC)CC)C>C(#N)C.O1CCCC1>[NH:1]([C:8]1[S:9][C:10]([C:13]2[CH2:20][S:19][CH:18]3[N:15]([C:16](=[O:29])[CH:17]3[NH:21][C:22](=[O:23])[CH2:56][C:52]3[S:51][CH:55]=[CH:54][CH:53]=3)[C:14]=2[C:30]([O:32][CH:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:31])=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 13175942HCID 13175942, compound

Product 1

HCID 13175960HCID 13175960, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Anilinothiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2.3 g) is treated with methanesulphonic acid (2.3 cc) in acetonitrile (23 cc) by following the procedure described in Reference Example 1. This gives crude 7-amino-3-(2-anilinothiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.85 g), which is acylated with (thien-2-yl)-acetyl chloride (0.445 cc) in tetrahydrofuran (25 cc), in the presence of triethylamine (0.505 cc), by following the procedure described in Reference Example 1. The crude product obtained is chromatographed on a column (height: 30 cm; diameter: 2.5 cm) of silica gel (0.04-0.06 mm), elution being carried out under a pressure of 1.2 bars (120 kPa) with a 70/30 (by volume) mixture of cyclohexane and ethyl acetate (3 liters), and 50 cc fractions being collected. Fractions 20 to 50 are combined and concentrated to dryness. After trituration in isopropyl ether, 3-(2-anilinothiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-7-(thien-2-yl-acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.9 g) is obtained in the form of a yellow solid.

Workup

  1. customThis gives crude 7-amino-3-(2-anilinothiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.85 g), which
  2. customThe crude product obtained
  3. customis chromatographed on a column (height: 30 cm; diameter: 2.5 cm) of silica gel (0.04-0.06 mm), elution
  4. additionbeing carried out under a pressure of 1.2 bars (120 kPa) with a 70/30 (by volume) mixture of cyclohexane and ethyl acetate (3 liters), and 50 cc fractions
  5. custombeing collected
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f27070098a6a40c2bfa19906dbd552a2
Source dataset
uspto-grants-1985_07
Patent number
US04526962

Reaction notes

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