1,2-Dichloroethane → 4-[2-(Imidazol-2-yl)ethyl]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester acetate

HRID 583688Notes

Reaction equation

HRID 583688 reaction equation
Cl.[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][CH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1.Cl.[NH2:19][CH2:20][C@H:21]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[C:13]([OH:15])(=[O:14])[CH3:12].[C:25]([O:24][C:22](=[O:23])[C@@H:21]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH2:20][NH:19][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][C:3]2[NH:2][CH:6]=[CH:5][N:4]=2)=[CH:17][CH:16]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochlorideHCID 676956464-[2-(Imidazol-2-yl)ethyl]benzoic acid hydrochloride

Product 1

HCID 867543374-[2-(Imidazol-2-yl)ethyl]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acid 23-5 (ca 2 mmol), amine 2-1 (700 mg, 2.0 mmol), HOBT (324 mg, 2.4 mmol), and NMM (0.77 mL, 7.0 mmol) were combined in 10 mL DMF at -15°, then EDC (364 mg, 1.9 mmol) was added The mixture was warmed to RT, stirred overnight, then concentrated. Flash chromatography (silica, 4:1:1 CH2Cl2 /MeOH/HOAc) provided 23-6, Rf 0.22 (silica, 4:1:1 CH2Cl2 :MeOH:HOAc).

Workup

  1. concentrationconcentrated
  2. customFlash chromatography (silica, 4:1:1 CH2Cl2 /MeOH/HOAc) provided 23-6, Rf 0.22 (silica, 4:1:1 CH2Cl2 :MeOH:HOAc)

Sources & evidence

ORD record
ord-62989eaa1423487aa2cff4ee25f181b4
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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