Trifluoroacetic acid → HCID 178448478, compound

HRID 582489Notes

Reaction equation

HRID 582489 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:41]/[O:42]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:15]([NH:17][C@@H:18]2[C:25](=[O:26])[N:24]3[C@@H:19]2[S:20][CH2:21][C:22](/[CH:30]=[C:31]2/[C:32](=[O:40])[N:33]([CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:34][CH2:35]/2)=[C:23]3[C:27]([OH:29])=[O:28])=[O:16])[N:13]=1.C([SiH](CC)CC)C>C(OCC)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:41]/[OH:42])/[C:15]([NH:17][C@@H:18]2[C:25](=[O:26])[N:24]3[C@@H:19]2[S:20][CH2:21][C:22](/[CH:30]=[C:31]2/[C:32](=[O:40])[N:33]([CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:34][CH2:35]/2)=[C:23]3[C:27]([OH:29])=[O:28])=[O:16])[N:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 140400324HCID 140400324, compound

Product 1

HCID 178448478HCID 178448478, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

16.8 ml (219.4 mmol) Trifluoroacetic acid was cooled to 0° C., and 2.0 g (2.62 mmol) (6R,7R)-7-[(Z)-2-(2-amino-thiazol-4-yl)-2-trityloxyimino-acetylamino]-3-[(E)-1-isobutyl-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid were added portionwise, keeping the temperature below 5° C. After 5 min. at that temperature, 0.96 ml (6.06 mmol) of triethylsilane were added dropwise and the reaction mixture was stirred for 1 h at 0° C. During this time a beige suspension was formed which was poured with stirring into 100 ml of diethyl ether. After 1 h the crystals were collected by filtration and retreated with 50 ml diethyl ether. After 1.5 hours the product was filtered and dried under high vacuum.

Workup

  1. customthe temperature below 5° C
  2. customDuring this time a beige suspension was formed which
  3. additionwas poured
  4. filtrationAfter 1 h the crystals were collected by filtration
  5. filtrationAfter 1.5 hours the product was filtered
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-dc2520fd894f4b18b295e5d30d514282
Source dataset
uspto-grants-1999_07
Patent number
US05925632

Reaction notes

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