Dicyclohexylcarbodiimide → HCID 88485782, compound

HRID 2371671Notes

Reaction equation

HRID 2371671 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][CH:13]([C:22]([O:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:21])[CH:15]=2)/[C:8]([OH:10])=[O:9])[N:6]=1.C1(N=C=NC2CCCCC2)CCCCC1.O[N:54]1[C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=2[N:56]=[N:55]1>O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][CH:13]([C:22]([O:24][CH:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:21])[CH:15]=2)/[C:8]([O:10][N:54]2[C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=3[N:56]=[N:55]2)=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14100520HCID 14100520, compound

Product 1

HCID 88485782HCID 88485782, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(2-aminothiazol-4-yl)-2-(Z)-[diphenylmethyloxycarbonyl(3,4-dihydroxyphenyl)methyl]oxyiminoacetic acid (IIa) (779 mg, 1.5 mmol) [for the preparation of compound IIa see: Japan Kokai 88-99078 published 4/30/88], dicyclohexylcarbodiimide (DCC, 352 mg, 1.71 mmol), N-hydroxybenzotriazole (261 mg, 1.71 mmol) in tetrahydrofuran (THF) (6 ml) was stirred at room temperature for 1 hr and the resulting precipitate was filtered off. The filtrate was concentrated under reduced pressure to provide 1.00 gram (100%) of the activated ester IIIa.

Workup

  1. customfor the preparation of compound
  2. filtrationthe resulting precipitate was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae4850675f1f44dc8dab18274660c476
Source dataset
uspto-grants-1992_03
Patent number
US05095012

Reaction notes

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