2-Thiopheneacetyl chloride → HCID 69468827, compound

HRID 1597703Notes

Reaction equation

[NH2:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6](/[CH:14]=[C:15]1/[C:16](=[O:24])[N:17]([CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH2:18][CH2:19]/1)=[C:7]2[C:11]([OH:13])=[O:12].C(=O)(O)[O-].[Na+].[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][C:36](Cl)=[O:37]>CN(C)C=O>[CH:21]1([CH2:20][N:17]2[CH2:18][CH2:19]/[C:15](=[CH:14]\[C:6]3[CH2:5][S:4][C@H:3]4[N:8]([C:9](=[O:10])[C@H:2]4[NH:1][C:36](=[O:37])[CH2:35][C:31]4[S:30][CH:34]=[CH:33][CH:32]=4)[C:7]=3[C:11]([OH:13])=[O:12])/[C:16]2=[O:24])[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 300.0 mg (0.86 mmol) (E)-(6R,7R)-7-amino-3-(1-cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid in 8 ml N,N-dimethylformamide was added 80.0 mg (0.95 mmol) sodium bicarbonate. After cooling to 0° C. 101.0 μl (0.95 mmol) 2-thiopheneacetyl chloride were added. After 1.5 h the solvent was stripped off at a rotary evaporator and the residue was poured on diethyl ether. The solid was collected by filtration and was triturated with 25 ml ethyl acetate and 15 ml water for 1.5 h.

Workup

customAfter 1.5 h the solvent was stripped off at a rotary evaporator
additionthe residue was poured on diethyl ether
filtrationThe solid was collected by filtration
customwas triturated with 25 ml ethyl acetate and 15 ml water for 1.5 h.

Sources & evidence

ORD record: ord-304236c5ebeb47e094d5494cb7816937
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06294668B1

Reaction notes

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