Diisopropylethylamine → HCID 89725486, compound

HRID 925299Notes

Reaction equation

HRID 925299 reaction equation
[CH2:1]([O:4][C:5]([C:7]1([CH2:12][CH2:13][C:14]([OH:16])=O)[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3].[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:40])[O:25][CH2:26][CH:27]1[C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:29]1[C:28]2[CH:27]([CH2:26][O:25][C:24]([NH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:14](=[O:16])[CH2:13][CH2:12][C:7]3([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH2:8][CH2:9][CH2:10][CH2:11]3)=[O:40])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]=2[CH:32]=[CH:31][CH:30]=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 89725802HCID 89725802, compound

Product 1

HCID 89725486HCID 89725486, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(1-(allyloxycarbonyl)cyclopentyl)propanoic acid (1.191 g, 5.26 mmol) in 40 ml DMF was added (9H-fluoren-9-yl)methyl 5-aminopentylcarbamate (2.049 g, 6.32 mmol), DIEA (4.60 mL, 26.3 mmol) and HATU (2.402 g, 6.32 mmol). After stirring for 10 minutes, DMF was removed under reduced pressure. The material was subjected to normal-phase purification using a gradient of 0-100% acetonitrile in DCM. Fractions containing the desired material were combined and solvent removed under reduced pressure to give crude allyl 1-(3-(5-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentylamino)-3-oxopropyl)cyclopentanecarboxylate (360 mg, 0.676 mmol, 12.84% yield) that was used in the next step without further purification.

Workup

  1. customDMF was removed under reduced pressure
  2. customThe material was subjected to normal-phase purification
  3. additionFractions containing the desired material
  4. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-60ca926885f14ea0a5cfa6d300ccf54b
Source dataset
uspto-grants-2016_03
Patent number
US09284283B2

Reaction notes

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