Glycine tert-butyl ester → 2-(3-((3-((4-(Piperidin-1-yl)-2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)benzyl)thio)propanamido)acetic acid

HRID 1407994Notes

Reaction equation

HRID 1407994 reaction equation
[NH2:1][CH2:2][C:3]([O:5]C(C)(C)C)=[O:4].[F:10][C:11]([F:57])([F:56])[C:12]1[CH:13]=[C:14]([CH:53]=[CH:54][CH:55]=1)[CH2:15][NH:16][C:17]([C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]2[CH:30]=[C:29]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH:28]=[CH:27][C:26]=2[NH:37][C:38]([C:40]2[CH:41]=[C:42]([CH:50]=[CH:51][CH:52]=2)[CH2:43][S:44][CH2:45][CH2:46][C:47](O)=[O:48])=[O:39])[CH:20]=1)=[O:18].O1CCN(CCNC(=O)CCSCC2C=C(C=CC=2)C(NC2C=CC(N3CCCCC3)=CC=2C2C=C(C=CN=2)C(NCC2C=CC=C(C(F)(F)F)C=2)=O)=O)CC1>ClCCl.C(O)(C(F)(F)F)=O>[N:31]1([C:29]2[CH:28]=[CH:27][C:26]([NH:37][C:38]([C:40]3[CH:41]=[C:42]([CH:50]=[CH:51][CH:52]=3)[CH2:43][S:44][CH2:45][CH2:46][C:47]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:48])=[O:39])=[C:25]([C:21]3[CH:20]=[C:19]([C:17](=[O:18])[NH:16][CH2:15][C:14]4[CH:53]=[CH:54][CH:55]=[C:12]([C:11]([F:57])([F:10])[F:56])[CH:13]=4)[CH:24]=[CH:23][N:22]=3)[CH:30]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 151417Glycine tert-butyl esterHCID 566494063-(3-((2-(4-((3-(Trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoic acidHCID 665867712-(2-(3-(((3-((2-Morpholinoethyl)amino)-3-oxopropyl)thio)methyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

Product 1

HCID 665879982-(3-((3-((4-(Piperidin-1-yl)-2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)benzyl)thio)propanamido)acetic acid

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Tert-butyl glycinate was coupled to 3-(3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)-benzylthio)propanoic acid 1.1 using the procedure described for the synthesis of 2-(2-(3-(((3-((2-morpholinoethyl)amino)-3-oxopropyl)thio)methyl)benzamido)-5-(piperidin-1-yl)-phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide 4.16. This material was dissolved in 2 mL of 1:1 dichloromethane/TFA and stirred for 1 h. The solvent was evaporated to give 4.6 mg of product. MS (ES, m/z): 734 [M+H]+

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9c380ee489df4a68a58ae68bad8e035d
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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