1,2-Dichloroethane → 2,5,6,10,13-Pentaazatetradecanedioic acid, 8-hydroxy-12-(1-methylethyl)-3-(1-methylpropyl)-4,11-dioxo-9-(phenylmethyl)-6-((4-(2-thiazolyl)phenyl)methyl)-, dimethyl ester, (3S-(3R*(R*),8R*,9R*,12R*))-

HRID 1873262Notes

Reaction equation

HRID 1873262 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11]([OH:13])=O)[C@H:7]([CH2:9][CH3:10])[CH3:8])=[O:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[S:28]1[CH:32]=[CH:31][N:30]=[C:29]1[C:33]1[CH:38]=[CH:37][C:36]([CH2:39][N:40]([NH2:64])[CH2:41][C@H:42]([OH:63])[C@@H:43]([NH:51][C:52](=[O:62])[C@H:53]([CH:59]([CH3:61])[CH3:60])[NH:54][C:55]([O:57][CH3:58])=[O:56])[CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:35][CH:34]=1>CN(C=O)C>[S:28]1[CH:32]=[CH:31][N:30]=[C:29]1[C:33]1[CH:34]=[CH:35][C:36]([CH2:39][N:40]([NH:64][C:11](=[O:13])[C@H:6]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:41][C@H:42]([OH:63])[C@@H:43]([NH:51][C:52](=[O:62])[C@H:53]([CH:59]([CH3:61])[CH3:60])[NH:54][C:55]([O:57][CH3:58])=[O:56])[CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:37][CH:38]=1

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 28378062L-Isoleucine, N-(methoxycarbonyl)-

Product 1

HCID 4679632,5,6,10,13-Pentaazatetradecanedioic acid, 8-hydroxy-12-(1-methylethyl)-3-(1-methylpropyl)-4,11-dioxo-9-(phenylmethyl)-6-((4-(2-thiazolyl)phenyl)methyl)-, dimethyl ester, (3S-(3R*(R*),8R*,9R*,12R*))-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Analogously to Example 7, 106 mg (0.56 mmol) of N-methoxycarbonyl-(L)-iso-leucine, 201 mg (1.05 mmol) of EDC and 95 mg (0.7 mmol) of HOBT in 4.6 ml of DMF and 293 μl (2.1 mmol) of TEA are reacted with 0.35 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 to form the title compound: m.p: 227-229° C.; HPLC20-100 : tRet =14.5; FAB MS (M+H)+ =697.

Sources & evidence

ORD record
ord-75ee7d4bdff54fa0931d647c5aaa4246
Source dataset
uspto-grants-2000_08
Patent number
US06110946

Reaction notes

Loading…