Diisopropylethylamine → Dibenzo[b,f]oxepine-10-carboxylic acid ((1S,2R)-1-benzyl-4-[bis-(4-ethyl-benzyl)-amino]-2-hydroxy-butyl}-amide

HRID 1432344Notes

Reaction equation

HRID 1432344 reaction equation
[NH2:1][C@H:2]([C@H:10]([OH:32])[CH2:11][CH2:12][N:13]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH3:31])=[CH:26][CH:25]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:33]1[C:43]2[CH:42]=[C:41]([C:44](O)=[O:45])[C:40]3[CH:47]=[CH:48][CH:49]=[CH:50][C:39]=3[O:38][C:37]=2[CH:36]=[CH:35][CH:34]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>>[CH2:3]([C@H:2]([NH:1][C:44]([C:41]1[C:40]2[CH:47]=[CH:48][CH:49]=[CH:50][C:39]=2[O:38][C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:43]=2[CH:42]=1)=[O:45])[C@H:10]([OH:32])[CH2:11][CH2:12][N:13]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH3:31])=[CH:28][CH:29]=1)[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH3:22])=[CH:19][CH:20]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 859640Dibenzo[b,f]oxepine-10-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68890594(2S,3R)-2-Amino-5-[bis-(4-ethyl-benzyl)-amino]-1-phenyl-pentan-3-ol

Product 1

HCID 86612521Dibenzo[b,f]oxepine-10-carboxylic acid ((1S,2R)-1-benzyl-4-[bis-(4-ethyl-benzyl)-amino]-2-hydroxy-butyl}-amideYield 34.4%

Procedure

A solution of (2S,3R)-2-Amino-5-[bis-(4-ethyl-benzyl)-amino]-1-phenyl-pentan-3-ol (13 mg), salt with two trifluoroacetic acids, Dibenzo[b,f]oxepine-10-carboxylic acid (5 mg), HBTU (11 mg) and N-Ethyl-diisopropylamine (0.007 ml in 2 ml DCM) is stirred for 16 h at rt. The reaction mixture is evaporated and purified by flash chromatography with hexane/EtOAc/NH3=3/1/0.01. 4.7 mg of desired product are obtained.

Workup

  1. customThe reaction mixture is evaporated
  2. custompurified by flash chromatography with hexane/EtOAc/NH3=3/1/0.01

Sources & evidence

ORD record
ord-e9b55a01618a4d2a820f2126d36b7b94
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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