Tetrahydrofuran → HCID 178502813, compound

HRID 1770195Notes

Reaction equation

[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:48][O:49][CH3:50])[C:27]([NH:29][C@@H:30]2[C:37](=[O:38])[N:36]3[C@@H:31]2[CH2:32][S:33][C:34]([CH2:46][Cl:47])=[C:35]3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:51]1([P:57]([C:64]2C=[CH:68][CH:67]=[CH:66][CH:65]=2)[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.O1CCC[CH2:71]1>>[Cl-:47].[C:2]1([C:1]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:48]/[O:49][CH3:50])/[C:27]([NH:29][C@@H:30]3[C:37](=[O:38])[N:36]4[C@@H:31]3[CH2:32][S:33][C:34]([C:46]3[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=3[P+:57]([CH3:71])([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[C:35]4[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:28])[N:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 11776Triphenylphosphine

HCID 57179529HCID 57179529, compound

Product 1

HCID 178502813HCID 178502813, compound

Conditions

Temperature: 20 °C

Procedure

2.182 g of 1,1-dimethylethyl (6S,7S) 7-[-2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-3-chloromethyl-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate, prepared as in Step G of reference Example B and 1.679 g of triphenyl phosphine were dissolved in 24 ml of tetrahydrofuran, and 14.1 g of silica were added. The tetrahydrofuran was distilled off under reduced pressure over 2 hours and the remainder was cooled, stirred for 26 hours at 20° C. then chromatographed over silica (eluent, dichloromethane-methanol, 9/11) to obtain 1.89 g of (6S,7S) 7-[(2-triphenylmethylaminothiazol-4-yl)-2-(Z)-methoxyimino-acetamido]-2-[(1,1-dimethylethyl)-oxycarbonyl]-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-3-yl-methyl-triphenyl-phosphonium chloride.

Workup

addition14.1 g of silica were added
distillationThe tetrahydrofuran was distilled off under reduced pressure over 2 hours
temperaturethe remainder was cooled
customthen chromatographed over silica (eluent, dichloromethane-methanol, 9/11)

Sources & evidence

ORD record: ord-ed5019e31d8b426ca69e1eb680463389
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05385897

Reaction notes

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