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

HRID 55767

反応式

HRID 55767 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a1fc588f2049422e98b62bbc955960d0
出典データセット
uspto-grants-2016_09
特許番号
US09433600B2

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