Trifluoroacetic acid → HCID 131710347, compound

HRID 1658714Notes

Reaction equation

HRID 1658714 reaction equation
C([O:5][C:6]([C:8]1[N:13]2[C:14](=[O:24])[CH:15]([NH:16][C:17](=[S:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@H:12]2[S:11][CH2:10][C:9]=1[CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=[O:7])(C)(C)C.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[C:6]([C:8]1[N:13]2[C:14](=[O:24])[CH:15]([NH:16][C:17](=[S:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@H:12]2[S:11][CH2:10][C:9]=1[CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)([OH:7])=[O:5]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 131710349HCID 131710349, compound

Product 1

HCID 131710347HCID 131710347, compound

Procedure

4-t-Butoxycarbonyl-7-carboxymethylthioacetamido-3-(3-pyridylmethyl)ceph-3-em (XLIV) (250 mg.) was dissolved in trifluoroacetic acid (3 ml.) and allowed to stand at room temperature for 15 mins. The trifluoroacetic acid was stripped off under reduced pressure and the last traces removed by additions of dry toluene and reevaporation. The residue was taken up in acetone (1 ml.) and the small amount of insoluble material discarded. The title compound (XLV) ws precipitated by careful addition of the acetone solution to dry ether (10 ml.). It was an off-white non-crystalline powder (150 mg., 54%);

Workup

  1. customthe last traces removed by additions of dry toluene and reevaporation
  2. customThe title compound (XLV) ws precipitated by careful addition of the acetone solution to dry ether (10 ml.)

Sources & evidence

ORD record
ord-da485aebf95c4174949ff1c463c1b6e3
Source dataset
uspto-grants-1976_06
Patent number
US03966718

Reaction notes

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