Hydrochloric Acid → HCID 131711399, compound

HRID 2163260Notes

Reaction equation

HRID 2163260 reaction equation
C([O:3][CH2:4][C:5]1[CH:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:9]2[C:18](=[O:29])[C@@H:19]([NH:20][C:21](=[O:28])[CH2:22][C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)[C@H:8]2[S:7][CH:6]=1)=O.Cl.C1OC1C>CO>[OH:3][CH2:4][C:5]1[CH:10]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[N:9]2[C:18](=[O:29])[C@@H:19]([NH:20][C:21](=[O:28])[CH2:22][C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)[C@H:8]2[S:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6378Propylene OxideHCID 131711400HCID 131711400, compound

Product 1

HCID 131711399HCID 131711399, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

t-Butyl (6R,7R)-3-formyloxymethyl-7-(2-thienylacetamido)ceph-2-em-4-carboxylate (50 mg.; 0.115 mmole), warm methanol (2 ml) and 2N hydrochloric acid (0.025 ml) were stirred together at 25° C. at an apparent pH of 2. T.l.c. after 2 hours 20 minutes showed a virtually complete reaction. Propylene oxide (0.1 ml) was added and the mixture was stirred at 25° C. for 5 minutes. The mixture was partitioned between ethyl acetate (40 ml) and water (40 ml). The aqueous layer was extracted with ethyl acetate (20 ml) and the combined organic layers were washed with water (2 × 20 ml) and dried over anhydrous sodium sulphate and filtered and evaporated to a gum. This gum was dissolved in ethyl acetate (2 ml) and added dropwise to stirred 40 to 60° petroleum ether (100 ml) to give a pale yellow solid (23mg.; 50%). T.l.c. after work up indicated approximately 20% lactone. τ (d6DMSO) 0.81 (d, J 9Hz; NH), 2.6, 3.0 (mult.; thienyls), 3.5 (broad s; Δ2 2-H), 4.51 (d,d J 9, 5Hz; 7-H), 4.80 (d, J 5Hz; 6-H), 4.92 (broad s; --CH2OH), 5.10 (broad s; 4-H), 5.95 (mult; 3 CH2), 6.20 (s; ##STR5## and 8.55 (s; tBu).

Workup

  1. customa virtually complete reaction
  2. stirringthe mixture was stirred at 25° C. for 5 minutes
  3. customThe mixture was partitioned between ethyl acetate (40 ml) and water (40 ml)
  4. extractionThe aqueous layer was extracted with ethyl acetate (20 ml)
  5. washthe combined organic layers were washed with water (2 × 20 ml)
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customevaporated to a gum
  9. dissolutionThis gum was dissolved in ethyl acetate (2 ml)
  10. additionadded dropwise
  11. stirringto stirred 40 to 60° petroleum ether (100 ml)
  12. customto give a pale yellow solid (23mg.; 50%)

Sources & evidence

ORD record
ord-bf430e7ab0f1494e8b02b06142ec2c9b
Source dataset
uspto-grants-1979_01
Patent number
US04132849

Reaction notes

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