1-Piperazinecarboxylic acid, ethyl ester → 4-[(S)-2-tert-Butoxycarbonylamino-4-(2H-tetrazol-5-yl)-butyryl]-piperazine-1-carboxylic acid ethyl ester

HRID 1970513Notes

Reaction equation

HRID 1970513 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][C:15]1[N:16]=[N:17][NH:18][N:19]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:53]([O:55][C:56]([N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1)=[O:57])[CH3:54]>CN(C=O)C>[CH2:53]([O:55][C:56]([N:58]1[CH2:59][CH2:60][N:61]([C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:14][C:15]2[N:16]=[N:17][NH:18][N:19]=2)[CH2:62][CH2:63]1)=[O:57])[CH3:54]

Participants

6

Reactant 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66855300(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-(1H-1,2,3,4-tetrazol-5-yl)butanoic acid

Product 1

HCID 668552454-[(S)-2-tert-Butoxycarbonylamino-4-(2H-tetrazol-5-yl)-butyryl]-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 82 mg (S)-2-tert-butoxycarbonylamino-4-(2H-tetrazol-5-yl)-butyric acid in 2 ml DMF were added 115 mg HATU, 100 μl DIPEA and 44 μl 1-ethoxycarbonyl-piperazine. After 1 h the solution was concentrated and the residue directly used in the next reaction step. Yield: 120 mg.

Workup

  1. concentrationAfter 1 h the solution was concentrated
  2. customthe residue directly used in the next reaction step

Sources & evidence

ORD record
ord-22cf2703ce004014bac48ac55189aad8
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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