Pyridine → HCID 70592094, compound

HRID 1707184Notes

Reaction equation

HRID 1707184 reaction equation
N1C=CC=CC=1.[OH:7][CH2:8][C:9]1[CH2:10][S:11][C@@H:12]2[C@H:32]([NH:33][C:34](=[O:41])[CH2:35][C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)[C:31](=[O:42])[N:13]2[C:14]=1[C:15]([O:17][CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].[C:43](Cl)(=[O:48])[C:44]([CH3:47])([CH3:46])[CH3:45]>O1CCCC1>[C:43]([O:7][CH2:8][C:9]1[CH2:10][S:11][C@@H:12]2[C@H:32]([NH:33][C:34](=[O:41])[CH2:35][C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)[C:31](=[O:42])[N:13]2[C:14]=1[C:15]([O:17][CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])(=[O:48])[C:44]([CH3:47])([CH3:46])[CH3:45]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 390251HCID 390251, compound

Product 1

HCID 70592094HCID 70592094, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of pyridine (2.4 ml.) in dry tetrahydrofuran (5 ml.) was added to a stirred solution of diphenylmethyl 3-hydroxymethyl-7β-(thien-2-yl)acetamido-ceph-3-em-4-carboxylate (3.12 g) and pivaloyl chloride (7.2 g) in dry tetrahydrofuran (150 ml) at 20°. The solution was stirred at 20° for 16 hours, filtered and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed successively with sodium bicarbonate solution, 2 N-hydrochloric acid, sodium bicarbonate solution, water and brine. The dried solution was concentrated under reduced pressure to give a solid residue that was triturated with ether to give the title ester (2.7 g; 75%), [α]D +5.1 (c 1.4, CHCl3), λinflex. (ethanol) 235 (ε14,100), 257 (ε8,300) and 263 nm. (ε8,050), λmax. (CHBr3) 1787 (β-lactam), 1722 (ester), 1680 and 1510 cm.-1 (CONH) τ (CDCl3) values include 8.81 (singlet; C(CH3)3).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed successively with sodium bicarbonate solution, 2 N-hydrochloric acid, sodium bicarbonate solution, water and brine
  5. concentrationThe dried solution was concentrated under reduced pressure
  6. customto give a solid residue that
  7. customwas triturated with ether

Sources & evidence

ORD record
ord-6ffb5f542ef447989e698999ad1c7407
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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