Morpholine → HCID 89725607, compound

HRID 925300Notes

Reaction equation

HRID 925300 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:39])[CH2:26][CH2:27][C:28]3([C:33]([O:35]CC=C)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.N1CCOCC1>CN(C=O)C.C([Pd](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:39])[CH2:26][CH2:27][C:28]3([C:33]([OH:35])=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32]3)=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 89725486HCID 89725486, compound

Product 1

HCID 89725607HCID 89725607, compoundYield 16.34%

Reagents, catalysts & solvents 2

HCID 178420201HCID 178420201, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Allyl 1-(3-(5-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentylamino)-3-oxopropyl)cyclopentanecarboxylate (360 mg, 0.676 mmol) was dissolved in DMF (15 mL) and cooled to 0° C. under nitrogen. Tetratritylpalladium (122 mg, 0.113 mmol) and morpholine (941 mg, 10.8 mmol) were added and the mixture stirred for 2 h. Solvent was removed under reduced pressure and material was purified by reverse-phase chromatography. Recovered 1-(3-(5-(((9H-fluoren-9-yl)methoxy)carbonylamino)pentylamino)-3-oxopropyl)cyclopentanecarboxylic acid (54.4 mg, 0.110 mmol, 16.34% yield).

Workup

  1. customSolvent was removed under reduced pressure and material
  2. customwas purified by reverse-phase chromatography

Sources & evidence

ORD record
ord-4bd819092db448708a286dbf1ffb7778
Source dataset
uspto-grants-2016_03
Patent number
US09284283B2

Reaction notes

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