Water → HCID 131720177, compound

HRID 1376848Notes

Reaction equation

HRID 1376848 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.[C:17]([NH:36][C:37]1[S:38][CH:39]=[C:40]([C:42](=[N:72][O:73][CH3:74])[C:43]([NH:45][CH:46]2[C:53](=[O:54])[N:52]3[CH:47]2[CH2:48][S:49][C:50]([SH:71])=[C:51]3[C:55]([O:57][CH:58]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[O:56])=[O:44])[N:41]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(Cl)Cl>[C:17]([NH:36][C:37]1[S:38][CH:39]=[C:40]([C:42](=[N:72][O:73][CH3:74])[C:43]([NH:45][C@H:46]2[C:53](=[O:54])[N:52]3[C@@H:47]2[CH2:48][S:49][C:50]([S:71][CH2:3][CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)=[C:51]3[C:55]([O:57][CH:58]([C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)[C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)=[O:56])=[O:44])[N:41]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 88373911HCID 88373911, compound

Product 1

HCID 131720177HCID 131720177, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

85 mg of N-chloroethyl pyrrolidine hydrochloride, 2 ml of methylene chloride and 210 μl of triethylamine were mixed together and 412 mg of diphenylmethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-mercapto-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate in 3 ml of methylene choride was added. The mixture was refluxed for 3 hours and after cooling to 20° C., the reaction mixture was poured into 10 ml of iced water. The mixture was stirred for 5 minutes, decanted and re-extracted with methylene chloride. The combined organic phases were dried and concentrated to dryness under reduced pressure. The residue was chromatographed on silica and eluted with a mixture of methylene chloride and acetone (1-1). After taking up again in isopropyl ether, 157 mg of syn isomer of racemic cis diphenylmethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-[(2-(1-pyrrolidinyl)-ethyl)-thio]-8-oxo-4-thia-1-azabicyclo [4,2,0]oct-2-en-2-carboxylate were obtained.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customdecanted
  3. extractionre-extracted with methylene chloride
  4. customThe combined organic phases were dried
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was chromatographed on silica
  7. washeluted with a mixture of methylene chloride and acetone (1-1)

Sources & evidence

ORD record
ord-d43a0fc4fba8476b8612bb5fd814ac54
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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