Isocyanate → HCID 131710765, compound

HRID 2398144Notes

Reaction equation

HRID 2398144 reaction equation
[CH2:1](CC(O)=O)[CH3:2].[C:7]([O:10][CH2:11][C:12]1[CH2:13][S:14][C@@H:15]2[C@H:22]([NH:23][C:24](=[O:34])[C:25](=[N:32][OH:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:21](=[O:35])[N:16]2[C:17]=1[C:18]([OH:20])=[O:19])(=[O:9])[CH3:8].[N-:36]=[C:37]=[O:38]>>[C:7]([O:10][CH2:11][C:12]1[CH2:13][S:14][C@@H:15]2[C@H:22]([NH:23][C:24](=[O:34])[C:25](=[N:32][O:33][C:37](=[O:38])[NH:36][CH2:1][CH3:2])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:21](=[O:35])[N:16]2[C:17]=1[C:18]([OH:20])=[O:19])(=[O:9])[CH3:8]

Participants

3

Reactant 2

HCID 105034IsocyanateHCID 131710766HCID 131710766, compound

Product 1

HCID 131710765HCID 131710765, compoundYield 47%

Procedure

To ethyl ioscyanate (5 ml.) was added (3-acetoxymethyl-7β-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylic acid ethyl acetate solvate (syn-isomer) (0.9 g.) and the mixtue stirred for one hour at room temperature. Two further portions of the isocyanate (5 ml.) were added, over a period of 2 hours. The mixture was then allowed to stand for 1 hour, and poured into petroleum (b.p. 40°-60°; 250 ml.) and the resulting precipitate collected, washed thoroughly with petroleum and dried. The solid was dissolved in ethyl acetate and extracted into sodium bicarbonate solution; the bicarbonate solution was then washed with ethyl acetate, acidified (2N-hydrochloric acid) and extracted with ethyl acetate. The combined extracts were dried and concentrated, and the concentrate (ca. 5 ml.) added dropwise to petroleum spirit with vigorous stirring. The precipitate formed was filtered and dried, giving the title acid (0.4 g., 47%), [α]D + 50° (c 0.85, DMSO), νmax. (pH 6 buffer) 257.5 nm (ε 21,200), νmax. (Nujol) 1782 (β-lactam), 1675 and 1520 cm.-1 (CONH), τ (DMSO-d6) values include 0.04 (doublet J 8 Hz; NH), 2.0-2.6 (multiplet; aromatic protons), 6.7-7.1 (multiplet; NHCH2CH3) and 8.89 (triplet, J 9 Hz; (CH2CH3).

Workup

  1. waitto stand for 1 hour
  2. customthe resulting precipitate collected
  3. washwashed thoroughly with petroleum
  4. customdried
  5. dissolutionThe solid was dissolved in ethyl acetate
  6. extractionextracted into sodium bicarbonate solution
  7. washthe bicarbonate solution was then washed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. customThe combined extracts were dried
  10. concentrationconcentrated
  11. concentrationthe concentrate (ca. 5 ml.)
  12. additionadded dropwise to petroleum spirit with vigorous stirring
  13. customThe precipitate formed
  14. filtrationwas filtered
  15. customdried

Sources & evidence

ORD record
ord-9c982270df7e463aa58bb13cacef2a87
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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