1,2-Dichloroethane → 1-[4-(Thiazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[N-(N-methoxycarbonyl-(L)-iso-leucyl)amino]-6-phenyl-2-azahexane

HRID 1873255Notes

Reaction equation

HRID 1873255 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11](O)=[O:12])[C@H:7]([CH2:9][CH3:10])[CH3:8])=[O:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[S:28]1[C:32]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][N:40]([NH2:65])[CH2:41][C@H:42]([OH:64])[C@@H:43]([NH:51][C:52](=[O:63])[C@H:53]([C@H:59]([CH2:61][CH3:62])[CH3:60])[NH:54][C:55]([O:57][CH3:58])=[O:56])[CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[CH:35][CH:34]=2)=[CH:31][N:30]=[CH:29]1>CN(C=O)C>[CH3:62][CH2:61][C@@H:59]([C@H:53]([NH:54][C:55]([O:57][CH3:58])=[O:56])[C:52]([NH:51][C@H:43]([C@@H:42]([OH:64])[CH2:41][N:40]([NH:65][C:11]([C@@H:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[C@H:7]([CH2:9][CH3:10])[CH3:8])=[O:12])[CH2:39][C:36]1[CH:35]=[CH:34][C:33]([C:32]2[S:28][CH:29]=[N:30][CH:31]=2)=[CH:38][CH:37]=1)[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:63])[CH3:60]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 28378062L-Isoleucine, N-(methoxycarbonyl)-HCID 665780011-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-amino-5 (S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane

Product 1

HCID 4679581-[4-(Thiazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[N-(N-methoxycarbonyl-(L)-iso-leucyl)amino]-6-phenyl-2-azahexane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Analogously to Example 7, 175 mg (0.92 mmol) of N-methoxycarbonyl-(L)-iso-leucine, 332 mg (1.7 mmol) of EDC and 156 mg (1.15 mmol) of HOBT in 2.5 ml of DMF and 483 μl (3.47 mmol) of TEA are reacted with 0.578 mmol of 1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane (Example 11b) in 5.2 ml of DMF to form the title compound: m.p: 213-216° C.; HPLC20-100 : tRet =14.7; FAB MS (M+H)+ =711.

Sources & evidence

ORD record
ord-cd4a4c9acbd64d0885287df9185b5299
Source dataset
uspto-grants-2000_08
Patent number
US06110946

Reaction notes

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