1,2-Dichloroethane → HCID 23382062, compound

HRID 1281192Notes

Reaction equation

HRID 1281192 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11]([OH:13])=O)[C:7]([CH3:10])([CH3:9])[CH3:8])=[O:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:47]=[CH:46][C:45]([CH2:48][N:49]([NH2:73])[CH2:50][C@H:51]([OH:72])[C@@H:52]([NH:60][C:61](=[O:71])[C@H:62]([CH:68]([CH3:70])[CH3:69])[NH:63][C:64]([O:66][CH3:67])=[O:65])[CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[CH:44][CH:43]=2)[CH2:38][CH2:37]1>CN(C=O)C.C(OCC)(=O)C.C(O)C>[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:43]=[CH:44][C:45]([CH2:48][N:49]([NH:73][C:11](=[O:13])[C@H:6]([C:7]([CH3:8])([CH3:9])[CH3:10])[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:50][C@H:51]([OH:72])[C@@H:52]([NH:60][C:61](=[O:71])[C@H:62]([CH:68]([CH3:70])[CH3:69])[NH:63][C:64]([O:66][CH3:67])=[O:65])[CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[CH:46][CH:47]=2)[CH2:38][CH2:37]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11263950N-(Methoxycarbonyl)-L-tert-leucineHCID 233820841-[p-(4-methylpiperazin-1-yl)phenyl]-4(S)-hydroxy-2-amino-5(S)-[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane

Product 1

HCID 23382062HCID 23382062, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

129 mg (0.68 mmol) of N-methoxycarbonyl-(L)-tert-leucine, 244 mg (1.28 mmol) of EDC and 115 mg (0.85 mmol) of HOBT are initially introduced, under a N2 atmosphere, in 5.4 ml of DMF. After 20 min at RT, 0.355 ml (2.55 mmol) of triethylamine is added. 232 mg (0.425 mmol) of 1-[p-(4-methylpiperazin-1-yl)phenyl]-4(S)-hydroxy-2-amino-5(S)-[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane (Example 16g) are then added and the mixture is thoroughly stirred overnight; working-up then takes place in analogy with Example 16. Column chromatography (SiO2; ethyl acetate/ethanol 1:1) results in the title compound:

Workup

  1. waitthe mixture is thoroughly stirred overnight

Sources & evidence

ORD record
ord-c31087e738884239bc95be2478db82b3
Source dataset
uspto-grants-2002_09
Patent number
US06451973B1

Reaction notes

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