Dicyclohexylcarbodiimide → Fmoc-Gly-OPfp

HRID 393893

Reaction equation

HRID 393893 reaction equation
[NH:1]([C:6]([O:8][CH2:9][CH:10]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[CH2:2][C:3]([OH:5])=[O:4].O[C:24]1[C:33]([F:34])=[C:31]([F:32])[C:29]([F:30])=[C:27]([F:28])[C:25]=1[F:26].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:6]([O:8][CH2:9][CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[C:22]1=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:7])[CH2:2][C:3]([O:5][C:24]1[C:25]([F:26])=[C:27]([F:28])[C:29]([F:30])=[C:31]([F:32])[C:33]=1[F:34])=[O:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 93124Fmoc-Gly-OH

Product 1

HCID 2733282Fmoc-Gly-OPfp

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Fmoc-Gly-OH (891 mg, 3.0 mmol) and PfpOH(754 mg, 4.5 mmol) in DMF (12 mL) was added DCC (845 mg, 4.5 mmol) at 0° C. for 30 min and then room temperature for 15 h. The reaction mixture was filterd to remove DCUrea and the flitrate was evaporated in vacuo to give the crude Fmoc-Gly-OPfp. To a solution of Fmoc-Gly-OPfp and BocPNA-OH (436 mg, 2.0 mmol) in DMF (16 mL) was added diisoprppylethylamine (445 il, 2.6 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 (0-50% MeOH/CH2Cl2) to give Fmoc-Gly-BocPNA-OH (121 mg, 12%). 1H NMR (DMSO-d6) δ 7.88 (d, J=7.0 Hz, 2H), 7.72 (d, J=7.0 Hz, 2H), 7.62 (brt) and 7.56 (brt) (1H), 7.41 (t, J=7.0 Hz, 2H), 7.33 (t, J=7.0 Hz, 2H), 7.18 (m, 2H), 6.85 (brt) and 6.79 (brt) (1H), 4.35-4.15 (m, 3H), 4.05-3.85 (m, 3H), 3.77 (m, 1H), 3.40-3.25 (m, 2H), 3.10 (m) and 3.03 (s) (2H), 1.37 (brs, 9H); 13C NMR (DMSO-d6) δ 172.2 (d), 169.10 (d), 156.34 (d), 155.58 (d), 143.83, 140.66, 127.58, 127.04, 125.24, 120.04, 77.77 (d), 65.71, 47.34 (d), 46.72, 46.65 (d), 29.23 (d), 28.14 (d); FABMS m/z 498 [(M+H)+].

Workup

  1. customto remove DCUrea
  2. customthe flitrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c4cc8c272eb84cc2b48907990a8bad74
Source dataset
uspto-grants-2004_10
Patent number
US06809190B2

Linked notes

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