Carbon Tetrachloride → HCID 70246610, compound

HRID 1954012Notes

Reaction equation

HRID 1954012 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[OH:55])[C:5]([OH:47])=[C:6]([CH:46]=1)[CH2:7][C:8]1[C:9]([OH:45])=[C:10]([CH:42]=[CH:43][CH:44]=1)[C:11]([O:13][CH2:14][C:15]1[CH2:16][S:17][C@@H:18]2[CH:29]([NH:30][C:31](=[O:40])[CH2:32][O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28](=[O:41])[N:19]2[C:20]=1[C:21]([O:23]C(C)(C)C)=[O:22])=[O:12].C(Cl)(Cl)(Cl)Cl>C(C(O)=O)(F)(F)F.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[OH:55])[C:5]([OH:47])=[C:6]([CH:46]=1)[CH2:7][C:8]1[C:9]([OH:45])=[C:10]([CH:42]=[CH:43][CH:44]=1)[C:11]([O:13][CH2:14][C:15]1[CH2:16][S:17][C@@H:18]2[CH:29]([NH:30][C:31](=[O:40])[CH2:32][O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28](=[O:41])[N:19]2[C:20]=1[C:21]([OH:23])=[O:22])=[O:12]

Participants

5

Reactant 2

HCID 5943Carbon TetrachlorideHCID 131721999HCID 131721999, compound

Product 1

HCID 70246610HCID 70246610, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 17 (3.93 g, 4.99 mmol) in CF3CO2H (35%) in CH2Cl2 (45 mL) was stirred at room temperature for 13 h. The solution was condensed under reduced pressure and then CCl4 (30 mL) was added to the residue and evaporated. The resultant solid was crystallized from a mixture of EtOH and ether (2:1) to afford pure 19 (3.28 g, 4.49 mmol) as a white crystal in 90% yield: mp 196-198° C.; 1H NMR (DMSO-d6 /D2O) d 3.60 (br s, 4H, 2×CH2), 3.68, 3.79 (AB, Jgem =19 Hz, 2H, CH2S), 4.65 (s, 2H, OCH2CO), 4.95, 5.21 (AB, Jgem =14 Hz, 2H, CH2O), 5.15 (d, J=5.1 Hz, 1H, HC(6)), 5.76 (d, J=5.1 Hz, 1H, HC(7)), 6.80-7.35 (m, 14H, 4×ArH); IR (nujol): 3300-3450 (OH, NH, CO2H), 1785 (β-lactam), 1720 (ester), 1685 (amide), 1610 (C=O) cm-1. Anal. (C37H31N2O10SCl) C, H, N, S Cl.

Workup

  1. customcondensed under reduced pressure
  2. customevaporated
  3. customThe resultant solid was crystallized from a mixture of EtOH and ether (2:1)

Sources & evidence

ORD record
ord-e3fd41291a2c41918ac7996b1a2e6d58
Source dataset
uspto-grants-2000_09
Patent number
US06121255

Reaction notes

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