Trifluoroacetic acid → 6,15-Bis(benzyloxy)-7-oxo-6,15-diazapentadecanenitrile

HRID 2380144Notes

Reaction equation

HRID 2380144 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:39])[N:24]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:25][CH2:26][CH2:27][CH2:28][C:29]#[N:30])=O)(C)(C)C.Cl.ON(C(=O)CCCCN(O)C(=O)CCCCN(O)C(=O)CCCCCCCCC)CCCCCN.CO.C(Cl)(Cl)Cl>C(Cl)Cl>[CH2:32]([O:31][N:24]([C:23](=[O:39])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[CH2:25][CH2:26][CH2:27][CH2:28][C:29]#[N:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 1041519115-(tert-Butoxycarbonyl)-6,15-bis(benzyloxy)-7-oxo-6,15-diazapentadecanenitrileHCID 189566656,12,18-Trihydroxy-7,13,19-trioxo-6,12,18-triazaoctacosanamine hydrochlorideHCID 21584188Chloroform methanol

Product 1

HCID 100725246,15-Bis(benzyloxy)-7-oxo-6,15-diazapentadecanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Excess TFA was added to [II] (2.00 g, 3.63 mmol) in CH2Cl2 at 0° C. The solution was stirred at 0° C. for 30 minutes and at room temperature for 15 minutes, and then the reaction was worked up by the method used for (5). Silica gel column chromatography with 2% MeOH/CHCl3 provided 1.51 g (92%) of [III] as an oil: NMR δ 1.17-1.90 (m, 14H), 2.23-2.50 (m, 4H), 2.90 (t, 2H, J=6), 3.40 (s, 1H), 3.63 (t, 2H, J=6), 4.67 (s, 2H), 4.77 (s, 2H), 7.30 (s, 5H), 7.33 (s, 5H). Anal. (C27H37N3O3) C, H, N.

Sources & evidence

ORD record
ord-aa6f66182884417eab9bf2cc7b34602a
Source dataset
uspto-grants-1994_11
Patent number
US05364965

Reaction notes

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