Dicyclohexylcarbodiimide → HCID 178450677, compound

HRID 895064Notes

Reaction equation

HRID 895064 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:13]2[C:14](=[O:17])[CH:15]([NH2:16])[C@H:12]2[S:11][CH2:10][C:9]=1[CH:18]([S:24][C:25]1[NH:29][N:28]=[N:27][N:26]=1)[CH2:19][CH2:20][C:21](=[O:23])[NH2:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:30][C:31]([F:41])([F:40])[CH2:32][S:33]([CH2:36][C:37](O)=[O:38])(=[O:35])=[O:34].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:1]([O:5][C:6]([C:8]1[N:13]2[C:14](=[O:17])[CH:15]([NH:16][C:37](=[O:38])[CH2:36][S:33]([CH2:32][C:31]([F:40])([F:30])[F:41])(=[O:34])=[O:35])[C@H:12]2[S:11][CH2:10][C:9]=1[CH:18]([S:24][C:25]1[NH:29][N:28]=[N:27][N:26]=1)[CH2:19][CH2:20][C:21](=[O:23])[NH2:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 205740432-(2,2,2-Trifluoroethanesulfonyl)acetic acidHCID 178450678HCID 178450678, compound

Product 1

HCID 178450677HCID 178450677, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8.4 g. (0.019 mol.) of 7-amino3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem4-carboxylic acid t-butyl ester and 3.9 g. (0.019 mol.) of 2,2,2-trifluoroethylsulfonylacetic acid in tetrahydrofuran is added dropwise a solution of 3.9 g. (0.019 mol.) of dicyclohexylcarbodiimide in 100 ml. of tetrahydrofuran. The reaction mixture is stirred at 25° for 12 hours, then filtered and concentrated to about 10 ml. The residue is filtered and evaporated to dryness to give 7-(2,2,2-trifluoroethylsulfonylacetamido)-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid t-butyl ester.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to about 10 ml
  3. filtrationThe residue is filtered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-f88f319b627a4ba984104ca09dc371c6
Source dataset
uspto-grants-1981_08
Patent number
US04286089

Reaction notes

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