Diethyl Ether → HCID 13367914, compound

HRID 1153932Notes

Reaction equation

HRID 1153932 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.IC[CH:9]=[CH:10][C:11]1[CH2:12][S:13][C@@H:14]2[CH:34]([NH:35][C:36](=[O:66])/[C:37](=[N:63]\[O:64][CH3:65])/[C:38]3[N:39]=[C:40]([NH:43]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:41][CH:42]=3)[C:33](=[O:67])[N:15]2[C:16]=1[C:17]([O:19]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:18].[CH3:68]COCC>>[NH2:43][C:40]1[S:41][CH:42]=[C:38](/[C:37](=[N:63]/[O:64][CH3:65])/[C:36]([NH:35][CH:34]2[C:33](=[O:67])[N:15]3[C:16]([C:17]([O-:19])=[O:18])=[C:11](/[CH:10]=[CH:9]/[CH2:1][N+:2]4([CH3:68])[CH2:6][CH2:5][CH2:4][CH2:3]4)[CH2:12][S:13][C@H:14]23)=[O:66])[N:39]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 84541-MethylpyrrolidineHCID 172930622HCID 172930622, compound

Product 1

HCID 13367914HCID 13367914, compound

Procedure

N-Methylpyrrolidine (0.2 ml, 2 mmole) was added to a suspension of diphenylmethyl 3-(3-iodo-1-propen-1-yl)-7-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylate (X-1, 958 mg, 1 mmole) in ether (100 ml) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, the filter cake was treated with 90% trifluoroacetic acid (5 ml) at room temperature for 1 hour, and the resulting mixture was concentrated under reduced pressure to give a light yellow powder (500 mg). The crude product was dissolved in formic acid (2 ml) and placed on a column of HP-20 resin (40 ml). The column was washed with water (about 500 ml) until the pH of the eluate became 7 and then was eluted with 30% aqueous CH3OH. The eluate was monitored by UV absorption at 254 nm. The fractions containing the desired product were combined, concentrated and lyophilized to give 185 mg of light yellow powder. It was purified by HPLC (Lichrosorb RP-18; 20% methanol) to give 101 mg (20%) of the title compound I-1A. M.p. >160° C. (dec.).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filter cake was treated with 90% trifluoroacetic acid (5 ml) at room temperature for 1 hour
  3. concentrationthe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7961ccfadf604187a12b9ec2ea7a6820
Source dataset
uspto-grants-1984_12
Patent number
US04486586

Reaction notes

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