Dicyclohexylcarbodiimide → Fmoc-Phe-Gly-NH-(CH2)6NH-Boc

HRID 55767

반응식

HRID 55767 반응식
[NH:1]([C:17]([O:19][CH2:20][CH:21]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[C@H:2]([C:10]([NH:12][CH2:13][C:14](O)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(N=C=NC2CCCCC2)CCCCC1.O.ON1C2C=CC=CC=2N=N1.[C:60]([NH:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][NH2:74])([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61]>C1COCC1>[NH:1]([C:17]([O:19][CH2:20][CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[C:33]1=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:18])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:74][CH2:73][CH2:72][CH2:71][CH2:70][CH2:69][CH2:68][NH:67][C:60]([O:62][C:63]([CH3:64])([CH3:65])[CH3:66])=[O:61])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 2733170N-BOC-1,6-diaminohexaneHCID 27960291-Hydroxybenzotriazole hydrateHCID 11328236Fmoc-Phe-Gly-OH

생성물 1

HCID 131733680Fmoc-Phe-Gly-NH-(CH2)6NH-Boc수율 94.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Fmoc-Phe-Gly-OH (0.66 g) in anhydrous THF (20 mL) at 0° C. under N2 was added N,N′-dicyclohexylcarbodiimide (0.307 g) and 1-hydroxybenzotriazole hydrate (0.201 g). After stirring for 15 min, N-Boc-1,6-diaminohexane (0.322 g) was added. The reaction mixture was allowed to warm to RT and stirred overnight. Solids were filtered off and they were washed with EtOAc. The filtrate and washings were then concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (0 to 10% MeOH in CH2Cl2) to afford Fmoc-Phe-Gly-NH—(CH2)6NH-Boc as a white solid (0.9 g).

후처리

  1. stirringstirred overnight
  2. filtrationSolids were filtered off
  3. washthey were washed with EtOAc
  4. concentrationThe filtrate and washings were then concentrated under reduced pressure
  5. customThe resulting residue was purified by flash column chromatography (0 to 10% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-a1fc588f2049422e98b62bbc955960d0
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433600B2

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