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

HRID 467354노트

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HRID 467354 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-19479433fbc3461c879e4c0ae89705b2
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05159061

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