1,2-Dichloroethane → 4-[2-(Indol-2-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine methyl ester

HRID 583660Notes

Reaction equation

HRID 583660 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1.Cl.[NH2:23][CH2:24][C@H:25]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32])[C:26]([O:28][CH3:29])=[O:27].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.CCOC(C)=O>[CH3:29][O:28][C:26](=[O:27])[C@@H:25]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32])[CH2:24][NH:23][C:17](=[O:19])[C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 158507584-[2-(Indol-2-yl)ethyloxy]benzoic acidHCID 22865877Methyl 3-Amino-2(S)-phenylsulfonylaminopropionate hydrochloride

Product 1

HCID 158507244-[2-(Indol-2-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acid 4-4 (100 mg, 0.36 mmol), amine 2-2 (105 mg, 0.36 mmol), EDC (88 mg., 0.46 mmol), HOBT (62 mg, 0.46 mmol) and NMM (137 μL, 1.2 mmol) were combined in 2 mL DMF. After 16 h the mixture was diluted with EtOAc, washed with water, sat. NaHCO3, 5% KHSO4, and brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 65% EtOAc/hexane) provided 4-5 as an oil. Rf 0.32 (silica, 65% EtOAc/hexane).

Workup

  1. washwashed with water, sat. NaHCO3, 5% KHSO4, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a9bc8cef434d4329a77a592a6471d847
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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