1,2-Dichloroethane → HCID 9810137, compound

HRID 1281181Notes

Reaction equation

HRID 1281181 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]([NH:12][C@H:13]([C:18]([OH:20])=O)[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:11].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:36]([N:38]([C:41]1[CH:46]=[CH:45][C:44]([CH2:47][N:48]([NH2:72])[CH2:49][C@H:50]([OH:71])[C@@H:51]([NH:59][C:60](=[O:70])[C@H:61]([CH:67]([CH3:69])[CH3:68])[NH:62][C:63]([O:65][CH3:66])=[O:64])[CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:43][CH:42]=1)[CH2:39][CH3:40])[CH3:37]>CN(C=O)C>[CH2:36]([N:38]([C:41]1[CH:46]=[CH:45][C:44]([CH2:47][N:48]([NH:72][C:18](=[O:20])[C@H:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[NH:12][C:10]([O:9][CH3:8])=[O:11])[CH2:49][C@H:50]([OH:71])[C@@H:51]([NH:59][C:60](=[O:70])[C@H:61]([CH:67]([CH3:68])[CH3:69])[NH:62][C:63]([O:65][CH3:66])=[O:64])[CH2:52][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)=[CH:43][CH:42]=1)[CH2:39][CH3:40])[CH3:37]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11263950N-(Methoxycarbonyl)-L-tert-leucineHCID 23382092HCID 23382092, compound

Product 1

HCID 9810137HCID 9810137, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In analogy with Example 2, 1.05 ml (7.5 mmol) of triethylamine are added to a solution of 0.37 g (2 mmol) of N-methoxycarbonyl-(L)-tert-leucine (Example 2h), 0.7 g (3.75 mmol) of EDC and 0.33 g (2.5 mmol) of HOBT in 8 ml of DMF and the whole is stirred at RT for 10 min. After that, 0.95 g (1.25 mmol) of 1-[p-(N,N-diethylamino)phenyl]-4(S)-hydroxy-2-amino-5(S)-[N-(N-methoxycarbonyl-(L)-valyl)amino]-6-phenyl-2-azahexane hydrochloride (Example 5b), dissolved in 2 ml of DMF, is added and the whole is stirred at RT for 2.75 h. The reaction mixture is evaporated under reduced pressure. After having been taken up in methylene chloride, the residue is washed consecutively with water, aqueous sodium bicarbonate and brine. The organic phase is then concentrated and the residue is digested in DIPE. The title compound is obtained after filtering off and drying.

Workup

  1. additionis added
  2. stirringthe whole is stirred at RT for 2.75 h
  3. customThe reaction mixture is evaporated under reduced pressure
  4. washthe residue is washed consecutively with water, aqueous sodium bicarbonate and brine
  5. concentrationThe organic phase is then concentrated

Sources & evidence

ORD record
ord-ad5e27cf89b041fe9f54f4c5ac1cf8df
Source dataset
uspto-grants-2002_09
Patent number
US06451973B1

Reaction notes

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