1,2-Dichloroethane → methyl N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]amino]-4-phenylbutyl]-2-[[4-(1,3-thiazol-2-yl)phenyl]methyl]hydrazinyl]-3-methyl-1-oxobutan-2-yl]carbamate

HRID 1276985Notes

Reaction equation

HRID 1276985 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10](O)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[S:27]1[CH:31]=[CH:30][N:29]=[C:28]1[C:32]1[CH:37]=[CH:36][C:35]([CH2:38][N:39]([NH2:63])[CH2:40][C@H:41]([OH:62])[C@@H:42]([NH:50][C:51](=[O:61])[C@H:52]([CH:58]([CH3:60])[CH3:59])[NH:53][C:54]([O:56][CH3:57])=[O:55])[CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:34][CH:33]=1>CN(C=O)C>[CH3:59][CH:58]([C@H:52]([NH:53][C:54]([O:56][CH3:57])=[O:55])[C:51]([NH:50][C@H:42]([C@@H:41]([OH:62])[CH2:40][N:39]([NH:63][C:10]([C@@H:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:7]([CH3:9])[CH3:8])=[O:11])[CH2:38][C:35]1[CH:34]=[CH:33][C:32]([C:28]2[S:27][CH:31]=[CH:30][N:29]=2)=[CH:37][CH:36]=1)[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:61])[CH3:60]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 106974131-[4-(Thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-valyl)amino6-phenyl-2-azahexaneHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 467965methyl N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]amino]-4-phenylbutyl]-2-[[4-(1,3-thiazol-2-yl)phenyl]methyl]hydrazinyl]-3-methyl-1-oxobutan-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Analogously to Example 7,140 mg (0.80 mmol) of N-methoxycarbonyl-(L)-valine, 288 mg (1.5 mmol) of EDC and 135 mg (1.0 mmol) of HOBT in 2.2 ml of DMF and 418 μl (3.0 mmol) of TEA are reacted with 0.5 mmol of 1-[4-(thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-valyl)amino-6-phenyl-2-azahexane in 4.5 ml of DMF to form the title compound: m.p: 207-210° C.; HPLC20-100 : tRet =13.8; FAB MS (M+H)+ =683.

Sources & evidence

ORD record
ord-c29ce6871ba94d7095a6511850c71b86
Source dataset
uspto-grants-2000_12
Patent number
US06166004

Reaction notes

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