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

HRID 705176

Reaction equation

HRID 705176 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-09d18dd09f7d495f84def42289717ea3
Source dataset
uspto-grants-2015_11
Patent number
US09173956B2

Linked notes

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