1,2-Dichloroethane → HCID 54061835, compound

HRID 1081377Notes

Reaction equation

HRID 1081377 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][S:9][CH2:10][C:11]([OH:13])=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:11](=[O:13])[CH2:10][S:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=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 242647[(4-nitrobenzyl)thio]acetic acidHCID 67553617HCID 67553617, compound

Product 1

HCID 54061835HCID 54061835, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-Nitrobenzylthio)acetic acid (68 mg, 300 μmol), dissolved in DMF (4 mL), was treated with HOBT (51 rag, 300 μmol), EDC (65 mg, 300 μmol), and N-[2(S)-amino-3-methylpentyl)-N-(1-naphthylmethyl)-glycyl-methionine methyl ester hydrochloride (133 mg, 250 μmol). The pH was adjusted to 7.5 with Et3N (110 μL, 250 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 provide the title compound. 1H NMR (CDCl3); δ0.89 (t, 3H, J=7.5 Hz), 0.91 (d, 3H, J=6.9 Hz), 1.02-1.19 (m, 1H), 1.37-1.6 (m, 2H), 1.67-1.79 (m, 1H), 1.85-1.98 (m, 1H), 1.95 (s, 3H), 2.0-2.1 (m, 3H), 2.74 (dd, 1H, J=3, 12 Hz), 2.86-3.01 (m, 3H), 3.21 (d, 1H, J=14 Hz), 3.29 (d, 1H, 14 Hz), 3.69 (s, 3H), 3.74 (d, 1H, J=12 Hz), 3.8 (d, 1H, J=12 Hz), 3.83-3.94 (m, 1H), 4.05 (d, 1H, J=9 Hz), 4.18 (d, 1H, J=9 Hz), 4.41-4.49 (m, 1H), 6.7 (d, 1H, J=8 Hz), 7.39-7.53 (m, 7H), 7.8-7.9 (m, 2H), 8.14-8.22 (m, 2H).

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-9990c4f854be4f18abe9cc325a14aaec
Source dataset
uspto-grants-1996_12
Patent number
US05585359

Reaction notes

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