Acetic Acid → Diphenylmethyl (6R,7R)-8-oxo-7-((phenylacetyl)amino)-3-((4-(pyridin-4-yl)-1,3-thiazol-2-yl)thio)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

HRID 1071317Notes

Reaction equation

HRID 1071317 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:39](=[O:40])[N:13]3[C:14]([C:23]([O:25][CH:26]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:24])=[C:15](OS(C)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].CO.[N:46]1[CH:51]=[CH:50][C:49]([C:52]2[N:53]=[C:54]([SH:57])[S:55][CH:56]=2)=[CH:48][CH:47]=1.C(O)(=O)C>O1CCCC1.O.CO>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:39](=[O:40])[N:13]3[C:14]([C:23]([O:25][CH:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:24])=[C:15]([S:57][C:54]4[S:55][CH:56]=[C:52]([C:49]5[CH:50]=[CH:51][N:46]=[CH:47][CH:48]=5)[N:53]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 11050121diphenylmethyl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 23694274Sodium methanolate methanolHCID 178527846HCID 178527846, compound

Product 1

HCID 68808181Diphenylmethyl (6R,7R)-8-oxo-7-((phenylacetyl)amino)-3-((4-(pyridin-4-yl)-1,3-thiazol-2-yl)thio)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-3 °C

Procedure

Benzhydryl 7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate-(900 g, 1.56 mol) was dissolved in tetrahydrofuran (3.6 L) and cooled to −3° C. While maintaining the same temperature, 28% sodium methylate-methanol solution (360 g, 1.87 mol) of 4-(4-pyridyl)-1,3-thiazole-2-thiol (362.5 g, 1.87 mol) obtained in the same manner as in Reference Example 29, and tetrahydrofuran (720 mL) solution were added. The mixture was stirred for 1.5 hr. Acetic acid (18.7 g) was added and after stirring for 30 min, methanol (9 L) and water (5.4 L) were added. The mixture was stirred for 2 hr. The precipitated crystals were collected by filtration, washed with methanol (16 L) and dried in vacuo. yield: 884 g (84%)

Workup

  1. additionwere added
  2. stirringafter stirring for 30 min
  3. stirringThe mixture was stirred for 2 hr
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with methanol (16 L)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d9b69423f16247eba91299ccb4152fd1
Source dataset
uspto-grants-2005_06
Patent number
US06906055B2

Reaction notes

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