Tetrahydrofuran → HCID 131712743, compound

HRID 1388486Notes

Reaction equation

HRID 1388486 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:32]2[N:33]=[C:34]([NH:37]C(=O)C(F)(F)F)[S:35][CH:36]=2)[C:9]([NH:11][CH:12]2[C:30](=[O:31])[N:14]3[C:15]([C:27]([OH:29])=[O:28])=[C:16]([CH2:19][S:20][C:21]4[N:25]([CH3:26])[N:24]=[N:23][N:22]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.O.C([O-])(=O)C.[Na+].O1CCCC1.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[CH:1]1([O:6][N:7]=[C:8]([C:32]2[N:33]=[C:34]([NH2:37])[S:35][CH:36]=2)[C:9]([NH:11][CH:12]2[C:30](=[O:31])[N:14]3[C:15]([C:27]([OH:29])=[O:28])=[C:16]([CH2:19][S:20][C:21]4[N:25]([CH3:26])[N:24]=[N:23][N:22]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 23665404Sodium Acetate TrihydrateHCID 131712744HCID 131712744, compound

Product 1

HCID 131712743HCID 131712743, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

7-[2-cyclopentyloxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.8 g) was added to a solution of sodium acetate trihydrate (5.8 g) in water (25 ml), and tetrahydrofuran (8.0 ml) was added thereto to give clear solution. The solution was stirred for 16 hours at ambient temperature. To the reaction mixture were added water and ethyl acetate and the mixture was adjusted to pH 6.2 with a saturated aqueous solution of sodium bicarbonate. The separated aqueous layer was washed twice with ethyl acetate and adjusted to pH 3.0 with 10% hydrochloric acid. Precipitates were collected by filtration, washed with water and dried under reduced pressure to give 7-[2-cyclopentyloxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.63 g), mp 152° to 154° C. (dec.).

Workup

  1. additionwas added
  2. customto give clear solution
  3. washThe separated aqueous layer was washed twice with ethyl acetate
  4. customPrecipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-854cf89964cd4941826c8e357b4d0a7c
Source dataset
uspto-grants-1984_02
Patent number
US04431643

Reaction notes

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