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Hydrochloric Acid → 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino]-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester

HRID 1707434
Notes
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Reaction equation

HRID 1707434 reaction equation
Cl.[C:2]1([CH:8]([O:15][C:16]([C:18]2[N:23]3[C:24](=[O:27])[C@@H:25]([NH2:26])[C@H:22]3[S:21][CH2:20][C:19]=2[O:28][S:29]([CH3:32])(=[O:31])=[O:30])=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33]([O:37][C:38]([NH:40][C:41]1[S:42][CH:43]=[C:44](/[C:46](=[CH:50]/[CH2:51][CH3:52])/[C:47](O)=[O:48])[N:45]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34].CN1CCOCC1.P(Cl)(Cl)(OC1C=CC=CC=1)=O.Cl>ClCCl>[C:2]1([CH:8]([O:15][C:16]([C:18]2[N:23]3[C:24](=[O:27])[C@@H:25]([NH:26][C:47](=[O:48])/[C:46](/[C:44]4[N:45]=[C:41]([NH:40][C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:39])[S:42][CH:43]=4)=[CH:50]\[CH2:51][CH3:52])[C@H:22]3[S:21][CH2:20][C:19]=2[O:28][S:29]([CH3:32])(=[O:31])=[O:30])=[O:17])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 13038Phosphorodichloridic acid, phenyl esterHCID 10334852(Z)-2-(2-t-butoxycarbonylamino-4-thiazolyl)pent-2-enoic acidHCID 883013187beta-Amino-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester hydrochloride

Product 1

HCID 88301235
7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino]-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester
Yield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7β-amino-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester hydrochloride (1.49 g: 3 mMol.) and (Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid (1.03 g: 3.45 mMol.) in dichloromethane (30 ml) is added at -30° C. N-methylmorpholine (1.1 ml : 10 mMol.) and, after 2 minutes, phenyl dichlorophosphate (0.49 ml: 3.27 mMol.), and the mixture is stirred at the same temperature for 1 hour and 20 minutes. The reaction mixture is mixed with 1N-hydrochloric acid (6 ml) and extracted with ethyl acetate. The extract is washed with water, aqueous 5% sodium hydrogen carbonate, and brine, dried over sodium sulfate, and concentrated. The residue (2.6 g) is dissolved in hot isopropanol (100 ml), cooled, and the separating pale yellow powder is collected by filtration to give 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino]-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester (2.01 g). Yield: 91%.

Workup

  1. additionis added at -30° C
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water, aqueous 5% sodium hydrogen carbonate, and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. dissolutionThe residue (2.6 g) is dissolved in hot isopropanol (100 ml)
  7. temperaturecooled
  8. filtrationthe separating pale yellow powder is collected by filtration

Sources & evidence

ORD record
ord-2180f07e6066477c8caf5d437094ddc0
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05352792

Reaction notes

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