1,2-Dichloroethane → 4-[2-(1-Benzyl-imidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester

HRID 583654Notes

Reaction equation

HRID 583654 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:36][CH2:37][C@H:38]([NH:46][S:47]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)(=[O:49])=[O:48])[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[C:42]([O:41][C:39](=[O:40])[C@@H:38]([NH:46][S:47]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)(=[O:49])=[O:48])[CH2:37][NH:36][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][C:11]2[N:10]=[CH:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:12]=2)=[CH:24][CH:23]=1)([CH3:45])([CH3:43])[CH3:44]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 158507574-[2-(N-Benzylimidazol-4-yl)ethyloxy]benzoic acidHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

Product 1

HCID 158507214-[2-(1-Benzyl-imidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 3-6 (147 mg, 0.46 mmol), HOBT (94 mg, 0.61 mmol), 2-1 (154 mg, 0.46 mmol), NMM (100 μL, 0.91 mmol), and DMF (1.2 mL) at 0° C. was treated with EDC (118 mg, 0.61 mmol) followed by removal of the cooling bath. The reaction pH was adjusted to 8 by addition of more NMM. After 20 h the reaction mixture was concentrated and the residue purified by to a flash chromatography column (silica, 9/0.5/0.5 CH2Cl2 /CH3OH/AcOH) to give 3-7 as a yellow solid after azeotropic removal of residual AcOH with toluene. Rf 0.48 (silica, 9/0.5/0.5 CH2Cl2 /CH3OH/AcOH).

Workup

  1. customfollowed by removal of the cooling bath
  2. additionThe reaction pH was adjusted to 8 by addition of more NMM
  3. concentrationAfter 20 h the reaction mixture was concentrated
  4. customthe residue purified by to a flash chromatography column (silica, 9/0.5/0.5 CH2Cl2 /CH3OH/AcOH)

Sources & evidence

ORD record
ord-598bdbbe2fe84fe1a0167b6bc7f97547
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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