1,2-Dichloroethane → HCID 131720983, compound

HRID 1458486Notes

Reaction equation

HRID 1458486 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([NH2:40])[CH2:16][C@H:17]([OH:39])[C@@H:18]([NH:26][C:27](=[O:38])[C@H:28]([C:34]([CH3:37])([CH3:36])[CH3:35])[NH:29][C:30]([O:32][CH3:33])=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:10][CH:9]=1.COC(N[C@H:46]([C:50]([OH:52])=O)[CH:47]([CH3:49])[CH3:48])=O.[CH2:53](Cl)CCl.C1C=CC2[N:65]([OH:66])N=NC=2C=1.CN([CH:70]=[O:71])C>>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([CH2:14][N:15]([NH:40][C:70](=[O:71])[C@H:49]([CH:47]([CH3:48])[CH:46]=[C:50]=[O:52])[NH:65][O:66][CH3:53])[CH2:16][C@H:17]([OH:39])[C@@H:18]([NH:26][C:27](=[O:38])[C@H:28]([C:34]([CH3:36])([CH3:37])[CH3:35])[NH:29][C:30]([O:32][CH3:33])=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228Dimethylformamide2×HCID 757711-HydroxybenzotriazoleHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 66578350HCID 66578350, compound

Product 1

HCID 131720983HCID 131720983, compound

Procedure

Analogously to Example 1, a solution of 0.964 g (1.5 mmol) of 1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)- tert-leucyl)amino-6-phenyl-2-aza-hexane hydrochloride in 10 ml of DMF is added dropwvise to a mixture of 0.42 g (2.4 mmol) of N-methoxycarbonyl-(L)-valine, 0.862 g (4.5 mmol) of EDC, 0.405 g (3 mmol) of HOBT and 1.26 ml of TEA in 10 ml of DMF. After working up, the crude product is digested in DIPE, filtered off and dried. Subsequent column chromatography (SiO2 ; hexane/ethyl acetate: 1/1 to 3/1) yields the pure title compound (TLC: Rf =0.35 (ethyl acetate); HPLC20-100 : tRet =10.9. FAB MS (M+H)+ =691.

Workup

  1. filtrationfiltered off
  2. customdried

Sources & evidence

ORD record
ord-b4b6c84d4dc14272bd8a118d2bb58b57
Source dataset
uspto-grants-1998_12
Patent number
US05849911

Reaction notes

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