Hydrochloric Acid → HCID 131714637, compound

HRID 1380970Notes

Reaction equation

HRID 1380970 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[O:64])[C:27]([NH:29][CH:30]2[C:62](=[O:63])[N:32]3[C:33]([C:46]([O:48][CH:49]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)=[O:47])=[C:34]([CH:37]=[CH:38][S:39][C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)[CH2:35][S:36][C@H:31]23)=[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.[BH4-].[Na+].Cl>CO.O1CCCC1>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([CH:26]([OH:64])[C:27]([NH:29][CH:30]2[C:62](=[O:63])[N:32]3[C:33]([C:46]([O:48][CH:49]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)=[O:47])=[C:34]([CH:37]=[CH:38][S:39][C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 131714638HCID 131714638, compound

Product 1

HCID 131714637HCID 131714637, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)glyoxylamido]-3-[2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate (syn isomer) (trans isomer) (3.1 g) in a mixture of methanol (16 ml) and tetrahydrofuran (16 ml) was added sodium borohydride (0.033 g) under ice-cooling and the mixture was stirred for 10 minutes. The reaction mixture was adjusted to pH 7.0 with 10% hydrochloric acid and extracted with ethyl acetate. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to give benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-hydroxyacetamido]-3-[2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate (trans isomer) (2.84 g).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-918b24d1d409492caa60900d14c96942
Source dataset
uspto-grants-1986_04
Patent number
US04584290

Reaction notes

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