Dimethylformamide → HCID 131726878, compound

HRID 2223036Notes

Reaction equation

HRID 2223036 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:10][N:11]1[C@@H:28]2[CH2:29][C:16]3[CH:17]=[CH:18][C:19]([O:31][CH3:32])=[C:20]4[O:21][C@H:22]5[C:23]([CH2:25][CH2:26][C@:27]2([OH:30])[C@:14]5([C:15]=34)[CH2:13][CH2:12]1)=[O:24].CN(C)C=O.CN1CCOCC1.[N:45]1(C(OC(C)(C)C)=O)[CH2:66][CH2:65][CH2:64][C@H:46]1[C:47]([N:49]1[CH2:63][CH2:62][CH2:61][C@H:50]1[C:51](ON1C(=O)CCC1=O)=[O:52])=[O:48]>>[NH:45]1[CH2:66][CH2:65][CH2:64][C@H:46]1[C:47]([N:49]1[CH2:63][CH2:62][CH2:61][C@H:50]1[C:51]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:52])=[O:48].[CH3:10][N:11]1[C@@H:28]2[CH2:29][C:16]3[CH:17]=[CH:18][C:19]([O:31][CH3:32])=[C:20]4[O:21][C@H:22]5[C:23]([CH2:25][CH2:26][C@:27]2([OH:30])[C@:14]5([C:15]=34)[CH2:13][CH2:12]1)=[O:24]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 14258383HCID 14258383, compoundHCID 131726879HCID 131726879, compound

Product 1

HCID 131726878HCID 131726878, compound

Procedure

To a solution of Leu-Oxycodone (1.0 eq) in dimethylformamide (10 ml/0.1 mmol) was added 4-methylmorpholine (10 eq) and Boc-Pro-Pro-OSu (2 eq). The reaction was stirred at ambient temperatures for 18 hours, quenched with water, and solvents removed. Crude protected product was purified using reverse phase HPLC. Deprotection occurred using 4N HCl in dioxane (20 ml/mmol) to obtain Pro-Pro-Leu-Oxycodone.

Workup

  1. customquenched with water, and solvents
  2. customremoved
  3. customwas purified

Sources & evidence

ORD record
ord-213ebe9fce7342789274aaf63b257a1d
Source dataset
uspto-grants-2008_05
Patent number
US07375083B2

Reaction notes

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