Dicyclohexylcarbodiimide → HCID 11363567, compound

HRID 393894Notes

Reaction equation

HRID 393894 reaction equation
[NH:1]([C:7]([O:9][CH2:10][CH:11]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].O[C:25]1[C:34]([F:35])=[C:32]([F:33])[C:30]([F:31])=[C:28]([F:29])[C:26]=1[F:27].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:7]([O:9][CH2:10][CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:8])[CH2:2][CH2:3][C:4]([O:6][C:25]1[C:26]([F:27])=[C:28]([F:29])[C:30]([F:31])=[C:32]([F:33])[C:34]=1[F:35])=[O:5]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 2724630N-Fluorenylmethoxycarbonyl-I2-alanine

Product 1

HCID 11363567HCID 11363567, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Fmoc-β-Ala-OH (311 mg, 1.0 mmol) and PfpOH(334 mg, 1.75 mmol) in DMF (2.5 mL) was added DCC (288 mg, 1.4 mmol) at 0° C. for 30 min and then room temperature for 15 h. The reaction mixture was filterd to remove DCUrea, the flitrate was evaporated in vacuo, and the residue was flush-chromatographed (CH2Cl2). The crude Fmoc-β-Ala-OPfp was recrystallized using hexane and CH2Cl2 to give the pure Fmoc-β-Ala-OPfp (429 mg 90%) as a white powder. To a solution of Fmoc-β-Ala-OPfp (100 mg, 0.21 mmol) and BocPNA-OH (41 mg, 0.19 mmol) in DMF (2 mL) was added diisoprppylethylamine (36 il, 0.21 mmol) and the reaction mixture was stirred at room temperature for 15 h. The reaction mixture was evaporated in vacuo and the residue was flush-chromatographed (0-10% MeOH/CH2Cl2) to give Fmoc-Gly-BocPNA-OH (41 mg, 42%). 1H NMR (DMSO-d6) δ 7.88 (d, J=7.4 Hz, 2H), 7.68 (d, J=7.4 Hz, 2H), 7.41 (t, J=7.3 Hz, 2H), 7.33 (t, J=7.3 Hz, 2H), 7.18 (m, 2H), 6.83 (brt) and 6.72 (brt) (2H), 4.3-4.2 (m, 4H), 4.05-3.9 (m, 3H), 3.33 (brt) and 3.29 (brt) (2H), 3.19 (m, 2H), 3.07 (brq) and 3.02 (brq) (2H), 1.36 (brs, 9H) ; 13C NMR (DMSO-d6) δ 171.20 (d), 170.85 (d), 155.93, 155.56, 143.87, 140.69, 127.55, 127.01, 125.09, 120.05, 77.73 (d), 65.30 (d), 59.69, 47.35 (d), 46.68, 46.49 (d), 37.99 (d), 36.72 (d), 28.14 (d).

Workup

  1. customto remove DCUrea
  2. customthe flitrate was evaporated in vacuo
  3. customthe residue was flush-chromatographed (CH2Cl2)
  4. customThe crude Fmoc-β-Ala-OPfp was recrystallized

Sources & evidence

ORD record
ord-682f5c2ff854464e9bb8c53b7b01ea7d
Source dataset
uspto-grants-2004_10
Patent number
US06809190B2

Reaction notes

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