Diisopropylethylamine → tert-Butyl 1-(3-{[(2S)-2-cyclopentyl-2-(4-methylphenyl)acetyl]amino}benzyl)cyclopropane-carboxylate

HRID 1475652Notes

Reaction equation

HRID 1475652 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH:34]1([C@@H:39]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=2)[C:40]([OH:42])=O)[CH2:38][CH2:37][CH2:36][CH2:35]1.[NH2:50][C:51]1[CH:52]=[C:53]([CH:65]=[CH:66][CH:67]=1)[CH2:54][C:55]1([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:57][CH2:56]1>CN(C=O)C>[CH:34]1([C@@H:39]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=2)[C:40]([NH:50][C:51]2[CH:52]=[C:53]([CH:65]=[CH:66][CH:67]=2)[CH2:54][C:55]2([C:58]([O:60][C:61]([CH3:64])([CH3:62])[CH3:63])=[O:59])[CH2:57][CH2:56]2)=[O:42])[CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 28293121(2S)-Cyclopentyl-(4-methylphenyl)acetic acidHCID 58136514tert-Butyl 1-(3-aminobenzyl)cyclopropanecarboxylate

Product 1

HCID 68006853tert-Butyl 1-(3-{[(2S)-2-cyclopentyl-2-(4-methylphenyl)acetyl]amino}benzyl)cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At RT, 453 mg (1191 μmol) of HATU and 479 μl (2750 μmol) of N,N-diisopropylethylamine were added to a solution of 200 mg (916 μmol) of (+)-(2S)-cyclopentyl(4-methylphenyl)acetic acid in 1 ml of DMF. The mixture was stirred for 30 min. 249 mg (1008 μmol) of tert-butyl 1-(3-aminobenzyl)cyclopropanecarboxylate were then added. The reaction mixture was stirred overnight and then directly separated into its components by preparative HPLC. This gave 328 mg (80% of theory) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customdirectly separated into its components by preparative HPLC

Sources & evidence

ORD record
ord-2bbd946e32d1453984a7954c15a4a0c7
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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