Pent-2-ynal → HCID 131715150, compound

HRID 979389Notes

Reaction equation

HRID 979389 reaction equation
[Br-].[C:2]1([CH:8]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[O:9][C:10]([C:12]2[N:17]3[C:18](=[O:23])[C@@H:19]([NH:20][CH:21]=[O:22])[C@H:16]3[S:15][CH:14](C[P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=2)=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:50](=O)(O)[O-].[Na+].[CH:55](=O)[C:56]#[C:57][CH2:58][CH3:59]>ClCCl>[CH:21]([NH:20][C@@H:19]1[C:18](=[O:23])[N:17]2[C:12]([C:10]([O:9][CH:8]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:11])=[C:13](/[CH:59]=[CH:58]\[C:57]#[C:56][CH2:55][CH3:50])[CH2:14][S:15][C@H:16]12)=[O:22]

Participants

5

Reactant 3

HCID 143255Pent-2-ynalHCID 516892Sodium BicarbonateHCID 131715151HCID 131715151, compound

Product 1

HCID 131715150HCID 131715150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of (6R,7R)-[4-diphenylmethoxycarbonyl-7-formamidoceph-3-em-ylmethyl]triphenylphosphonium bromide (15.00 g) (preparation described in British Patent Specification No. 1342241) in dichloromethane (250 ml) was treated with saturated sodium bicarbonate solution (75 ml). After a few minutes, 2-pentynal (3.28 g) was added, in one portion, and the mixture was stirred for ca 19 h. The two layers were separated and the organic phase was washed with 2N hydrochloric acid (250 ml), water (250 ml) and brine (250 ml) and dried (sodium sulphate). The solvent was removed and the residue was purified by chromatography (750 g silica gel). Elution with ethyl acetate:dichloromethane (1:19→1:14) gave the title compound as a solid (1.72 g); νmax (CHBr3) 3410 (NH), 2200 (C≡C), 1783 cm-1 (β-lactam); τ(CDCl3) values include 1.76 (H-CO), 3.26 (--CH=CH--C≡C), 3.54 (NH), 4.14 (7H), 4.42 (--CH=CH--C≡C), 4.98 (6H), 7.66 (C≡C--CH2 13 ).

Workup

  1. waitAfter a few minutes
  2. customThe two layers were separated
  3. washthe organic phase was washed with 2N hydrochloric acid (250 ml), water (250 ml) and brine (250 ml)
  4. dry with materialdried (sodium sulphate)
  5. customThe solvent was removed
  6. customthe residue was purified by chromatography (750 g silica gel)
  7. washElution with ethyl acetate:dichloromethane (1:19→1:14)

Sources & evidence

ORD record
ord-18de71cec36746d1a864693a31731857
Source dataset
uspto-grants-1987_05
Patent number
US04666899

Reaction notes

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