Morpholine → HCID 11599328, compound

HRID 1865702Notes

Reaction equation

HRID 1865702 reaction equation
[CH3:1][NH:2][C@H:3]([C:14]([NH:16][C@H:17]([C:22]([N:24]([C@@H:26]([CH:33]([CH3:35])[CH3:34])/[CH:27]=[C:28](/[C:30](O)=[O:31])\[CH3:29])[CH3:25])=[O:23])[C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15])[C:4]([CH3:13])([CH3:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[NH:58]1[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1>C(#N)C>[CH3:1][NH:2][C@H:3]([C:14]([NH:16][C@H:17]([C:22]([N:24]([C@@H:26]([CH:33]([CH3:35])[CH3:34])/[CH:27]=[C:28](\[CH3:29])/[C:30]([N:58]1[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1)=[O:31])[CH3:25])=[O:23])[C:18]([CH3:20])([CH3:21])[CH3:19])=[O:15])[C:4]([CH3:13])([CH3:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10435564HCID 10435564, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 11599328HCID 11599328, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

By using an analogous procedure to that described in General Procedure I Method A, N,β,β,3-tetramethyl-L-phenylalanyl-N1-[(1S,2E)-3-carboxy-1-isopropyl-2-butenyl]-N1,3-dimethyl-L-valinamide (100 mg, 0.205 mmol) is treated with hydroxybenzotriazole (36 mg, 0.27 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (59 mg, 0.31 mmol) in anhydrous acetonitrile (3 ml) at room temperature for 15 hours, followed by addition of morpholine (0.036 ml, 0.41 mmol). After stirring at room temperature for 15 hours, the product is purified using the aqueous work-up method, to provide the title compound (89 mg, 78%) as a orange amorphous solid.

Workup

  1. customthe product is purified

Sources & evidence

ORD record
ord-7b20cf5dfe4740ed886c7e8a4e4096f4
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Reaction notes

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