Dicyclohexylcarbodiimide → Boc-(D)Ala-Gly-OBzl

HRID 467354ノート

反応式

HRID 467354 の反応式
[NH2:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[NH:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:14]([C:16](O)=[O:17])[CH3:15].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>C(#N)C>[NH:13]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[C@@H:14]([C:16]([NH:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:17])[CH3:15]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 409140Benzyl glycinateHCID 637606BOC-D-alanine

生成物 1

HCID 15567200Boc-(D)Ala-Gly-OBzl

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To 7.4 g H-Gly-OBzl.p-Tos-OH, 100 ml acetonitrile was added, and this was followed by cooling with ice, then 3.1 ml TEA, 3.78 g Boc-D-Ala-OH, 3.96 g HONB and 4.54 g DCC were added, and this was followed by agitation for one night. The resulting DCU was filtered, and the filtrate was concentrated, then the resulting residue was dissolved in 300 ml AcOEt. The resulting solution was washed with 4% aqueous NaHCO3 and 10% aqueous citrate, after which it was dried with Na2SO4. The dried product, after concentration, was crystallized with petroleum benzine and collected by filtration.

後処理

  1. temperatureby cooling with ice
  2. waitthis was followed by agitation for one night
  3. filtrationThe resulting DCU was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionthe resulting residue was dissolved in 300 ml AcOEt
  6. washThe resulting solution was washed with 4% aqueous NaHCO3 and 10% aqueous citrate
  7. dry with materialafter which it was dried with Na2SO4
  8. concentrationThe dried product, after concentration
  9. customwas crystallized with petroleum benzine
  10. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-19479433fbc3461c879e4c0ae89705b2
出典データセット
uspto-grants-1992_10
特許番号
US05159061

反応ノート

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