Diethyl Ether → HCID 67121027, compound

HRID 1395949Notes

Reaction equation

HRID 1395949 reaction equation
[C:1](=[O:53])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:42])[C@@H:12]([NH:20][C:21](=[O:41])[C@@H:22]([NH:26][C:27](=[O:40])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]2[C:37](=[O:38])[CH:36]=[CH:35][C:34]2=[O:39])[CH:23]([CH3:25])[CH3:24])[CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH2:19])=[O:18])=[CH:6][CH:5]=1.[N:54]1([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]1.C(OCC)C>CS(C)=O>[O:39]=[C:34]1[CH:35]=[CH:36][C:37](=[O:38])[N:33]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][C:27]([NH:26][C@H:22]([C:21]([NH:20][C@H:12]([C:11]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][O:2][C:1]([N:57]2[CH2:56][CH2:55][N:54]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:59][CH2:58]2)=[O:53])=[CH:9][CH:8]=1)=[O:42])[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:18])[NH2:19])=[O:41])[CH:23]([CH3:24])[CH3:25])=[O:40]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 143452tert-Butyl piperazine-1-carboxylateHCID 57587849N-(6-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl)-L-valyl-N5-(aminocarbonyl)-N-(4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl)-L-ornithinamide

Product 1

HCID 67121027HCID 67121027, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Step 1 4-((S)-2-((S)-2-(6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl 4-nitrophenyl carbonate 58 (30 mg, 0.041 mmol) was reacted with tert-butyl piperazine-1-carboxylate (5.3 mg, 0.0287 mmol) in anhydrous DMSO under argon atmosphere at room temperature (FIG. 7d). The reaction mixture was stirred for 1 h, until disappearance of the starting material (HPLC-MS analysis). Diethyl ether (80 ml) was then added to the reaction mixture and the precipitate thus obtained was collected by filtration to give N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N-{4-[({[4-(tert-butoxycarbonyl)piperazin-1-yl]carbonyl}oxy)methyl]phenyl}-N5-carbamoyl-L-omithinamide 59 as a yellow solid, 22.0 mg) was isolated and used without further purification in the next step. MS (ESI): 785 [M+H]+. Retention time=4.87 min (method 1).

Workup

  1. customthe precipitate thus obtained
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-e3f7ee3623044353aa02ec2766c41e18
Source dataset
uspto-grants-2014_12
Patent number
US08900589B2

Reaction notes

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