Dimethylformamide → HCID 67437509, compound

HRID 467803Notes

Reaction equation

HRID 467803 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([OH:9])=O.[CH:10]([NH2:13])([CH3:12])[CH3:11].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN(C=O)C>C(Cl)Cl.CO.N>[CH:10]([NH:13][C:7]([C@@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:2]1[NH2:1])=[O:9])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6363IsopropylamineHCID 73305CispentacinHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 67437509HCID 67437509, compound

Reagents, catalysts & solvents 1

HCID 21584172Ammonia methanol dichloromethaneSolvent

Procedure

55 mg (0.43 mmol) cis-(±)-2-amino-cyclopentanecarboxylic acid are suspended in 900 μL (25 eq) isopropylamine and 205 mg (0.064 mmol, 1.5 eq) TBTU and 550 μL DMF are added. The mixture is stirred for 16 h and the reaction mixture is taken up in DCM/MeOH/NH3(aq) 9/1/0.1 and combined with 7 mL silica gel. After all the volatile constituents have been eliminated in vacuo the residue is chromatographed (silica gel DCM/MeOH/NH3 9/1/0.1). 63 mg of the title compound are obtained.

Workup

  1. customis chromatographed (silica gel DCM/MeOH/NH3 9/1/0.1)

Sources & evidence

ORD record
ord-c839e5a9a01f4e6eb00004bc367f7a67
Source dataset
uspto-grants-2014_01
Patent number
US08623887B2

Reaction notes

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