Methanesulfonic Acid → HCID 20430453, compound

HRID 2413414Notes

Reaction equation

HRID 2413414 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]([C:16]3[CH2:23][S:22][CH:21]4[N:18]([C:19](=[O:32])[CH:20]4[NH:24][C:25]([O:27]C(C)(C)C)=O)[C:17]=3[C:33]([O:35][CH:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:34])=[CH:14][N:15]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CS(O)(=O)=O.[S:54]1[CH:58]=[CH:57][CH:56]=[C:55]1[CH2:59]C(Cl)=O>C(#N)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]([C:16]3[CH2:23][S:22][CH:21]4[N:18]([C:19](=[O:32])[CH:20]4[NH:24][C:25](=[O:27])[CH2:59][C:55]4[S:54][CH:58]=[CH:57][CH:56]=4)[C:17]=3[C:33]([O:35][CH:36]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:34])=[CH:14][N:15]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 1623622-Thiopheneacetyl chlorideHCID 20430406HCID 20430406, compound

Product 1

HCID 20430453HCID 20430453, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

On treating 3-[2-(4-acetamido-phenyl)-thiazol-5-yl]-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (3.4 g) with methanesulphonic acid (3.4 cc) in acetonitrile (15 cc), in accordance with the working method described in Example 15, crude 7-amino-3-[2-(4-acetamido-phenyl)-thiazol-5-yl]-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2.9 g) is obtained, and this is acylated with (thien-2-yl)-acetyl chloride (0.62 cc) in accordance with the working method described in Example 1. The crude product obtained is purified by crystallisation from acetonitrile (200 cc). 3-[2-(4-Acetamido-phenyl)-thiazol-5-yl]-2-benzhydryloxycarbonyl-8-oxo-7-[(thien-2-yl)-acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.33 g) is obtained in the form of a beige crystalline powder.

Workup

  1. customcrude 7-amino-3-[2-(4-acetamido-phenyl)-thiazol-5-yl]-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2.9 g) is obtained
  2. customThe crude product obtained
  3. customis purified by crystallisation from acetonitrile (200 cc)

Sources & evidence

ORD record
ord-aa17b4f4708640f0b64409feffb1439c
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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