Triethylamine → (2S)-2-(2-(((Benzylcarbamoyl)amino)(prop-2-en-1-yl)amino)acetamido)-3-(4-(benzyloxy)-2-fluorophenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide

HRID 707494Notes

Reaction equation

HRID 707494 reaction equation
[NH2:1][C@@H:2]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][C:24]=1[F:37])[C:3]([N:5]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[N:8]=1)=[O:4].[CH2:38]([NH:45][C:46]([NH:48][N:49]([CH2:54][CH:55]=[CH2:56])[CH2:50][C:51](O)=[O:52])=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CO.C(OCC)(=O)C.ClCCl>[CH2:38]([NH:45][C:46]([NH:48][N:49]([CH2:54][CH:55]=[CH2:56])[CH2:50][C:51]([NH:1][C@@H:2]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:25][C:24]=1[F:37])[C:3]([N:5]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[N:8]=1)=[O:4])=[O:52])=[O:47])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594799102-(1-Allyl-2-(benzylcarbamoyl)hydrazinyl)acetic acidHCID 118162542(2S)-2-Amino-3-(4-(benzyloxy)-2-fluorophenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide

Product 1

HCID 118162453(2S)-2-(2-(((Benzylcarbamoyl)amino)(prop-2-en-1-yl)amino)acetamido)-3-(4-(benzyloxy)-2-fluorophenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamideYield 101.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of (2S)-2-amino-3-(4-(benzyloxy)-2-fluorophenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide (4.87 g, 9.48 mmol) described in Production Example 1-1-3 and dichloromethane (100 mL) were added a known substance (WO2009148192) 2-(((benzylcarbamoyl)amino)(prop-2-en-1-yl)amino)acetic acid (2.62 g, 9.95 mmol), triethylamine (2.64 mL, 19.0 mmol) and HBTU (3.96 g, 10.4 mmol) at room temperature. The resultant mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under a reduced pressure, and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate and then ethyl acetate:methanol=30:1) to give the title compound (7.28 g, yield: quantitative).

Workup

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. customthe resultant residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-86e4ac91ad7544778e2a471fafb0f80a
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

Loading…