Potassium Carbonate → benzhydryl (7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-3-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 2214767Notes

Reaction equation

HRID 2214767 reaction equation
[NH2:1][C:2]1[S:6][C:5]([SH:7])=[N:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:14]1([CH:20]([O:27][C:28]([C:30]2[N:31]3[CH:34]([CH2:35][CH2:36][C:37]=2Cl)[C@@H:33]([NH:39][C:40](=[O:70])/[C:41](/[C:63]2[N:64]=[C:65]([NH2:69])[S:66][C:67]=2[Cl:68])=[N:42]\[O:43][C:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:32]3=[O:71])=[O:29])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[C:14]1([CH:20]([O:27][C:28]([C:30]2[N:31]3[CH:34]([CH2:35][CH2:36][C:37]=2[S:7][C:5]2[S:6][C:2]([NH2:1])=[N:3][N:4]=2)[C@@H:33]([NH:39][C:40](=[O:70])/[C:41](/[C:63]2[N:64]=[C:65]([NH2:69])[S:66][C:67]=2[Cl:68])=[N:42]\[O:43][C:44]([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:32]3=[O:71])=[O:29])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 140482359benzhydryl (7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 178509208HCID 178509208, compound

Product 1

HCID 140482355benzhydryl (7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-3-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-amino-1,3,4-thiadiazole-2-thiol (0.6 g., 0.0045 mol) in dimethylformamide (25 mL) was added potassium carbonate (1.0 g, 0.0076 mol). The mixture was stirred for 1 hour at room temperature after which (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino]acetamido]-3-chloro-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate diphenylmethyl ester (3.2 g., 0.0039 mol) was added. Stirring was continued for 18 hours. The mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was separated, washed with water (30 mL), dried over anhydrous MgSO4 and the solvent was removed with a rotary evaporator. The resultant thick oil was treated with diethyl ether (50 mL) and the solid which formed was filtered and dried to give 2.6 g of crude product.

Workup

  1. additionwas added
  2. customThe mixture was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. customThe organic layer was separated
  4. washwashed with water (30 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customthe solvent was removed with a rotary evaporator
  7. additionThe resultant thick oil was treated with diethyl ether (50 mL)
  8. customthe solid which formed
  9. filtrationwas filtered
  10. customdried

Sources & evidence

ORD record
ord-87d4d2551d8541ab909acad345d46029
Source dataset
uspto-grants-2006_09
Patent number
US07109190B2

Reaction notes

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