Propylene Oxide → HCID 131711800, compound

HRID 1707179Notes

Reaction equation

HRID 1707179 reaction equation
[Cl:1][CH:2]([Cl:16])[C:3]([O:5][N:6]=[C:7]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:8](Cl)=[O:9])=[O:4].[C:17]([O:20][CH2:21][C:22]1[CH2:23][S:24][C@@H:25]2[C@H:36]([NH2:37])[C:35](=[O:38])[N:26]2[C:27]=1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])(=[O:19])[CH3:18].C1OC1C>C(OCC)(=O)C>[C:17]([O:20][CH2:21][C:22]1[CH2:23][S:24][C@@H:25]2[C@H:36]([NH:37][C:8](=[O:9])[C:7](=[N:6][O:5][C:3](=[O:4])[CH:2]([Cl:16])[Cl:1])[C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[C:35](=[O:38])[N:26]2[C:27]=1[C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 15573427tert-butyl (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 54155233HCID 54155233, compound

Product 1

HCID 131711800HCID 131711800, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-dichloroacetoxyimino-(thien-2-yl)acetyl chloride (syn-isomer) in ethyl acetate (300 ml.) was added to a stirred solution of t-butyl 3-acetoxymethyl-7β-aminoceph-3-em-4-carboxylate (43 g) and propylene oxide (34 ml.) in ethyl acetate (400 ml.) at 20°. Initially a solid precipitated out but it gradually redissolved. The temperature was maintained between 20° and 30° by alternately cooling and warming the solution. After 4 hours the solution was washed with 2 N-hydrochloric acid, saturated sodium bicarbonate solution, water and brine, and was dried and concentrated under reduced pressure to give the title ester as an oil that was used directly in the next stage.

Workup

  1. customInitially a solid precipitated out
  2. dissolutionit gradually redissolved
  3. temperatureThe temperature was maintained between 20° and 30°
  4. temperatureby alternately cooling
  5. temperaturewarming the solution
  6. washAfter 4 hours the solution was washed with 2 N-hydrochloric acid, saturated sodium bicarbonate solution, water and brine
  7. customwas dried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-28d0f60818f54342bfe4ca8609fd9789
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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