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

HRID 1970516Notes

Reaction equation

HRID 1970516 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:57][C:58]([N:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1)=[O:59])[CH2:54][CH2:55][CH3:56]>CN(C=O)C>[CH2:53]([O:57][C:58]([N:60]1[CH2:65][CH2:64][N:63]([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][CH2:61]1)=[O:59])[CH2:54][CH2:55][CH3:56]

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 21963126Butyl piperazine-1-carboxylateHCID 66855300(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-(1H-1,2,3,4-tetrazol-5-yl)butanoic acid

Product 1

HCID 668550864-[(S)-2-tert-Butoxycarbonylamino-4-(2H-tetrazol-5-yl)-butyryl]-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 222 mg (S)-2-tert-butoxycarbonylamino-4-(2H-tetrazol-5-yl)-butyric acid in 5 ml DMF were added 300 mg HATU, 541 μl DIPEA and 245 mg piperazine-1-carboxylic acid butyl ester hydrotrifluoroacetate. After 1 h the solution was concentrated, taken up with dichloromethane and washed with aqueous LiCl (4%) and 0.1 M HCl. The crude product thus obtained was used in the next reaction step without further purification.

Workup

  1. concentrationAfter 1 h the solution was concentrated
  2. washwashed with aqueous LiCl (4%) and 0.1 M HCl

Sources & evidence

ORD record
ord-0bd34675b8924cc287903f55d5c0811f
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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