1,2-Dichloroethane → methyl N-[(1S,2S)-1-[[(1S,2S)-1-benzyl-2-hydroxy-3-[[[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]amino]-[(4-thiazol-5-ylphenyl)methyl]amino]propyl]carbamoyl]-2-methyl-butyl]carbamate

HRID 380201Notes

Reaction equation

HRID 380201 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([OH:12])=O)[CH:7]([CH3:9])[CH3:8])=[O:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[S:27]1[C:31]([C:32]2[CH:37]=[CH:36][C:35]([CH2:38][N:39]([NH2:64])[CH2:40][C@H:41]([OH:63])[C@@H:42]([NH:50][C:51](=[O:62])[C@H:52]([C@H:58]([CH2:60][CH3:61])[CH3:59])[NH:53][C:54]([O:56][CH3:57])=[O:55])[CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:34][CH:33]=2)=[CH:30][N:29]=[CH:28]1>CN(C=O)C>[S:27]1[C:31]([C:32]2[CH:33]=[CH:34][C:35]([CH2:38][N:39]([NH:64][C:10](=[O:12])[C@H:6]([CH:7]([CH3:8])[CH3:9])[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:40][C@H:41]([OH:63])[C@@H:42]([NH:50][C:51](=[O:62])[C@H:52]([C@H:58]([CH2:60][CH3:61])[CH3:59])[NH:53][C:54]([O:56][CH3:57])=[O:55])[CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:36][CH:37]=2)=[CH:30][N:29]=[CH:28]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 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 467957methyl N-[(1S,2S)-1-[[(1S,2S)-1-benzyl-2-hydroxy-3-[[[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]amino]-[(4-thiazol-5-ylphenyl)methyl]amino]propyl]carbamoyl]-2-methyl-butyl]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 ml of DMF and 418 μL of TEA are reacted with 0.5 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 in 5 ml of DMF to form the title compound: m.p: 202-204° C.; HPLC20-100: tRet=14.0; FAB MS (M+H)+=697.

Sources & evidence

ORD record
ord-aa8ff4f5f724430d85ef38940cddeaf9
Source dataset
uspto-grants-2001_10
Patent number
US06300519B1

Reaction notes

Loading…