Trifluoroacetic acid → 11,22,33-Tris(benzyloxy)-12,15,23,26-tetraoxo-11,16,22,27,33-pentaaza-2,5,8-trioxatritriacontane

HRID 1656823Notes

Reaction equation

HRID 1656823 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]([O:68][CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:67])[CH2:23][CH2:24][C:25](=[O:66])[N:26]([O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:57])[CH2:34][CH2:35][C:36](=[O:56])[N:37]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH3:47])=O)(C)(C)C.C(ON(C(=O)CCC(=O)NCCCCCNOCC1C=CC=CC=1)CCCCC#N)C1C=CC=CC=1>C(Cl)Cl>[CH2:49]([O:48][N:37]([C:36](=[O:56])[CH2:35][CH2:34][C:33](=[O:57])[NH:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][N:26]([O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:25](=[O:66])[CH2:24][CH2:23][C:22](=[O:67])[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][O:68][CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH3:47])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10929123N1-(4-Cyanobutyl)-N1-(phenylmethoxy)-N4-[5-[(phenylmethoxy)amino]pentyl]butanediamideHCID 1510174033-(tert-Butoxycarbonyl)-11,22,33-tris(benzyloxy)-12,15,23,26-tetraoxo-11,16,22,27,33-pentaaza-2,5,8-trioxatritriacontane

Product 1

HCID 1510174111,22,33-Tris(benzyloxy)-12,15,23,26-tetraoxo-11,16,22,27,33-pentaaza-2,5,8-trioxatritriacontane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11,22,33-Tris(benzyloxy)-12,15,23,26-tetraoxo-11,16,22,27,33-pentaaza-2,5,8-trioxatritriacontane (21) was prepared by adding excess TFA to (20) (2.05 g, 2.16 mmol) in CH2Cl2 at 0° C. The solution was stirred at room temperature and worked up by the method of (9) to give 1.91 g (quantitative) of (21) as a waxy solid: NMR δ 1.18-1.70 (m, 12 H), 2.32-3.33 (m, 18 H), 3.39-3.80 (m, 14 H), 4.64 (s, 2 H), 4.80 (s, 2 H), 4.87 (s, 2 H), 6.23 (br s, 2 H), 7.2-7.4 (m, 15 H). Analysis: (C46H67N5O10.H2O) C, H, N.

Workup

  1. custom11,22,33-Tris(benzyloxy)-12,15,23,26-tetraoxo-11,16,22,27,33-pentaaza-2,5,8-trioxatritriacontane (21) was prepared

Sources & evidence

ORD record
ord-afb0e9efff1c47648113e97c09f726a8
Source dataset
uspto-grants-1993_10
Patent number
US05254724

Reaction notes

Loading…