Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1526672ノート

反応式

HRID 1526672 の反応式
N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@@H](C(O)=O)CCC(=O)[OH:6].[CH2:28]1[CH2:33][CH2:32][CH:31]([N:34]=[C:35]=[N:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH2:30][CH2:29]1>O1CCCC1>[CH:37]1([NH:36][C:35]([NH:34][CH:31]2[CH2:30][CH2:29][CH2:28][CH2:33][CH2:32]2)=[O:6])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

参加物

4

反応物 2

HCID 10868DicyclohexylcarbodiimideHCID 40501223N-FMOC-D-glutamic acid

生成物 1

HCID 4277N,N'-Dicyclohexylurea収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Fmoc-D-Glu-OH (59.8 g, 1.0 eq) was dissolved in anhydrous tetrahydrofuran (THF) (324 mL). DCC (40.1 g, 1.2 eq) was then added while stirring in ice-water bath. The reaction mixture was allowed to warm to r.t and stirring was maintained for additional 8 h to produce 1,3-dicyclohexylurea (DCU). The precipitates were filtered off, and washed with small amount THF. Dry ammonia gas was then bubbled through the filtrate which was stirred in a NaCl salt-ice bath. The reaction was completed after 1.5 h when no more white solid was precipitated. Still standing for 30 min, small amount MeOH was added to dissolve the solid. The mixture was cooled in an ice-water bath again. Then 2.0 N HCl was added carefully and slowly to adjust pH to 2-3. The solvent was evaporated under vacuum. The resulting solid was dissolved in AcOEt and then washed with diluted HCl, saturated aqueous NaHCO3 solution, and H2O sequentially. The organic layer was separated and combined, then dried with MgSO4 overnight, filtered and evaporated under vacuum. Then residue was recrystallized with ethylacetate-cyclohexane system. After filtration, 46.5 g target product was obtained with a yield of 78%. m.p.=204˜205° C., [α]=−4.2° (C=10 mg/mL, DMF).

後処理

  1. temperatureto warm
  2. temperaturewas maintained for additional 8 h

出典と根拠

ORDレコード
ord-beaf4fe5517d46afbce76f81fa792b29
出典データセット
uspto-grants-2015_07
特許番号
US09085605B2

反応ノート

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