Diisopropylethylamine → trans-1-(Tert-butoxycarbonyl)-4-(4-(4-(4-(6-(tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)pyrrolidine-3-carboxylic acid

HRID 2093752Notes

Reaction equation

HRID 2093752 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:45]=[CH:44][C:19]([CH2:20][NH:21][C:22]2[N:27]=[C:26]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[N:25]=[C:24]([NH:34][C:35]3[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][CH:36]=3)[N:23]=2)=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:46][C@@H:47]1[CH2:51][N:50]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:49][C@H:48]1[C:59]([OH:61])=[O:60].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>>[C:55]([O:54][C:52]([N:50]1[CH2:51][C@@H:47]([NH:46][C:39](=[O:40])[C:38]2[CH:37]=[CH:36][C:35]([NH:34][C:24]3[N:23]=[C:22]([NH:21][CH2:20][C:19]4[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])=[CH:45][CH:44]=4)[N:27]=[C:26]([O:28][CH2:29][C:30]([F:31])([F:33])[F:32])[N:25]=3)=[CH:43][CH:42]=2)[C@H:48]([C:59]([OH:61])=[O:60])[CH2:49]1)=[O:53])([CH3:58])([CH3:56])[CH3:57]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 40461048(3R,4S)-4-Amino-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acidHCID 670742404-(4-(4-(6-(Tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid

Product 1

HCID 67073843trans-1-(Tert-butoxycarbonyl)-4-(4-(4-(4-(6-(tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)pyrrolidine-3-carboxylic acidYield 12%

Procedure

To a solution of 4-(4-(4-(6-(tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid (200 mg), trans-4-amino-1-Boc-pyrrolidine-3-carboxylic acid (72.6 mg) and O-benzotriazol-1-yl-N,N,N′,N′-tetra-methyluronium tetrafluoroborate (121 mg) was added iPr2NEt (0.22 mL). The mixture was stirred at room temperature for 4 hours. The mixture was purified by preparative HPLC to give trans-1-(tert-butoxycarbonyl)-4-(4-(4-(4-(6-(tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)pyrrolidine-3-carboxylic acid (32 mg).

Workup

  1. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-751d5b2210ac4967807f929e96b3fdb6
Source dataset
uspto-grants-2013_05
Patent number
US08445490B2

Reaction notes

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