Dicyclohexylcarbodiimide → HCID 178468126, compound

HRID 1763473Notes

Reaction equation

HRID 1763473 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[C:18]([CH2:28][PH:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([S:22][C:23]1[NH:27][N:26]=[N:25][N:24]=1)[O:19][CH2:20][CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:36][C:37]([F:47])([F:46])[CH2:38][S:39]([CH2:42][C:43](O)=[O:44])(=[O:41])=[O:40].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:1]([O:5][C:6]([C:8]1[N:13]2[C:14](=[O:17])[C@@H:15]([NH:16][C:43](=[O:44])[CH2:42][S:39]([CH2:38][C:37]([F:46])([F:36])[F:47])(=[O:40])=[O:41])[C@H:12]2[S:11][CH2:10][C:9]=1[C:18]([CH2:28][PH:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])([S:22][C:23]1[NH:27][N:26]=[N:25][N:24]=1)[O:19][CH2:20][CH3:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 205740432-(2,2,2-Trifluoroethanesulfonyl)acetic acidHCID 178468127HCID 178468127, compound

Product 1

HCID 178468126HCID 178468126, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 10.42 g (0.019 mol) of 7-amino-3-(1-ethoxy-t-butoxyphosphinylmethyltetrazol-5-ylthiomethyl)-3-cephem-4-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 7β-(2,2,2-trifluoroethylsulfonylacetamido)-3-(1-ethoxy-t-butoxyphosphinylmethyltetrazol-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-daf7afe0281d438e9987d7a085c498b4
Source dataset
uspto-grants-1978_09
Patent number
US04112086

Reaction notes

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