1,2-Dichloroethane → HCID 54138481, compound

HRID 259970Notes

Reaction equation

HRID 259970 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[CH3:31][O:32][C:33](=[O:62])[C@H:34]([CH2:58][CH2:59][S:60][CH3:61])[NH:35][C:36](=[O:57])[CH2:37][N:38]([CH2:50][C@@H:51]([NH2:56])[CH:52]([CH3:55])[CH2:53][CH3:54])[CH2:39][C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1.CCN(CC)CC>CN(C=O)C>[CH3:31][O:32][C:33](=[O:62])[C@H:34]([CH2:58][CH2:59][S:60][CH3:61])[NH:35][C:36](=[O:57])[CH2:37][N:38]([CH2:50][C@@H:51]([NH:56][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[C@@H:52]([CH3:55])[CH2:53][CH3:54])[CH2:39][C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 797114-(4-Nitrophenyl)butyric acidHCID 67553617HCID 67553617, compound

Product 1

HCID 54138481HCID 54138481, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Nitrophenyl)butyric acid (73 mg, 350 μmol), dissolved in DMF (5 ml) was treated with HOBT (60 mg, 350 μmol), EDC (76 mg, 350 μmol) and N-[2(S)-amino-3-methylpentyl)-N-(1-naphthylmethyl)-glycyl-methionine methyl ester hydrochloride (160 mg, 300 μmol). The pH was adjusted to ~7.5 with Et3N (170 μl, 385 μmol) and the mixture was stirred at ambient temperature for 16 h. The mixture was concentrated and the residue was partitioned between EtOAc (100 ml) and H2O (100 ml). The organic layer was washed with H2O (2×50 ml), dried (MgSO4), filtered and concentrated to give a crude product which was purified by chromatography (silica gel, eluting with 1:1 to 1:2 hexane: EtOAc) to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between EtOAc (100 ml) and H2O (100 ml)
  3. washThe organic layer was washed with H2O (2×50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customwas purified by chromatography (silica gel, eluting with 1:1 to 1:2 hexane: EtOAc)

Sources & evidence

ORD record
ord-3158d2122d1846509c90ea07f60e7b03
Source dataset
uspto-grants-1996_06
Patent number
US05523456

Reaction notes

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