Diisopropylethylamine → HCID 89725392, compound

HRID 925298Notes

Reaction equation

HRID 925298 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:24])[O:9][CH2:10][CH:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:49]([O:53][C:54](=[O:65])[CH2:55][CH2:56][C:57]1([C:62](O)=[O:63])[CH2:61][CH2:60][CH2:59][CH2:58]1)([CH3:52])([CH3:51])[CH3:50].CCN(C(C)C)C(C)C>CN(C=O)C>[CH:13]1[C:12]2[CH:11]([CH2:10][O:9][C:8]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:62]([C:57]3([CH2:56][CH2:55][C:54]([O:53][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:65])[CH2:61][CH2:60][CH2:59][CH2:58]3)=[O:63])=[O:24])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2729672HCID 2729672, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11010130t-Butyl 3-(1-carboxycyclopentyl)propanoate

Product 1

HCID 89725392HCID 89725392, compoundYield 124.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (9H-fluoren-9-yl)methyl 5-aminopentylcarbamate (0.683 g, 2.105 mmol) in 15 ml DMF was added HATU (0.800 g, 2.105 mmol), 1-(3-tert-butoxy-3-oxopropyl)cyclopentanecarboxylic acid (0.425 g, 1.754 mmol) in 5 ml DMF, and DIEA (1.532 mL, 8.77 mmol). The solution was stirred for 10 minutes and material purified by HPLC using a gradient of 0-50% acetonitrile in DCM. Solvents were removed under reduced pressure to give 1.2 g crude tert-butyl 3-(1-(5-(((9H-fluoren-9-yl)methoxy)carbonylamino)-pentylcarbamoyl)cyclopentyl)propanoate. The crude material was dissolved in 20 ml DCM and 10 ml TFA was added to remove t-Bu group. Solvent was removed under reduced pressure and material purified by reverse phase chromatography to give 3-(1-(5-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentylcarbamoyl)cyclopentyl)propanoic acid (16 mg, 0.032 mmol, 1.852% yield).

Workup

  1. custommaterial purified by HPLC
  2. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-44c98c0a6837499f89c2bc199d8bb73c
Source dataset
uspto-grants-2016_03
Patent number
US09284283B2

Reaction notes

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