Phosphorus pentachloride → benzhydryl (6R)-3-(chloromethyl)-8-oxo-7-[[(2Z)-2-propan-2-yloxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1995935Notes

Reaction equation

HRID 1995935 reaction equation
[CH3:1][CH:2]([O:4]/[N:5]=[C:6](/[C:10]1[N:11]=[C:12]([NH:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:13][CH:14]=1)\[C:7]([OH:9])=O)[CH3:3].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:41][CH:42]1[C:67](=[O:68])[N:44]2[C:45]([C:51]([O:53][CH:54]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:52])=[C:46]([CH2:49][Cl:50])[CH2:47][S:48][C@H:43]12>ClCCl.C(OCC)(=O)C>[Cl:50][CH2:49][C:46]1[CH2:47][S:48][C@@H:43]2[CH:42]([NH:41][C:7](=[O:9])/[C:6](=[N:5]\[O:4][CH:2]([CH3:3])[CH3:1])/[C:10]3[N:11]=[C:12]([NH:15][C:16]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[S:13][CH:14]=3)[C:67](=[O:68])[N:44]2[C:45]=1[C:51]([O:53][CH:54]([C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52]

Participants

6

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 12784192(2Z)-2-propan-2-yloxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acidHCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 88490327benzhydryl (6R)-3-(chloromethyl)-8-oxo-7-[[(2Z)-2-propan-2-yloxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 107.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (Z)-2-(2-propoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (IVc) (707 mg, 1.5 mmoles) and phosphorus pentachloride (344 mg, 1.65 mmoles) in dichloromethane (14 mL) was stirred at room temperature for 1 hour and poured into a solution of Compound V (677 mg, 1.5 mmoles) and BSA (1.1 mL, 4.5 mmoles) in dichloromethane (15 mL). The reaction mixture was stirred at room temperature for 30 minutes, diluted with ethyl acetate (200 mL), washed with aqueous sodium bicarbonate (100 mL) and water (3×100 mL), dried over sodium sulfate and evaporated to give 1.4 g (100%) of Compound VIc.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  2. washwashed with aqueous sodium bicarbonate (100 mL) and water (3×100 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-fb1599e1d3294d7f8bbe4f48bcd9a317
Source dataset
uspto-grants-1983_09
Patent number
US04406899

Reaction notes

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