1,2-Dichloroethane → 4-Ethynylbenzoyl-2(S)-phenylsulfonylamino-beta-alanine ethyl ester

HRID 1599957Notes

Reaction equation

HRID 1599957 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[CH:2].[C:12]1(C)C=CC(S(O)(=O)=O)=C[CH:13]=1.C([NH:25][CH2:26][C@H:27]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C:28]([OH:30])=[O:29])C.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH2:12]([O:30][C:28](=[O:29])[C@@H:27]([NH:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:33])=[O:34])[CH2:26][NH:25][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:11][CH:10]=1)[CH3:13]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 5897064-Ethynylbenzoic acidHCID 86752459Ethyl 2(S)-phenylsulfonylamino-beta-alanine p-toluenesulfonate

Product 1

HCID 867524584-Ethynylbenzoyl-2(S)-phenylsulfonylamino-beta-alanine ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Ethynylbenzoic acid (35-1) (3.10 g, 21.2 mmol), 35-2 (8.58 g, 19.3 mmol), NMM (8.49 mL, 7.72 mmol), HOBT (3.39 g, 25.1 mmol), and EDC (4.81 g, 25.1 mmol) were combined in 96 mL DMF and stirred overnight. The reaction was concentrated, residue was diluted with EtOAc and washed with water (2×) and brine, dried (Na2SO4), filtered, and concentrated. Flash chromatography (silica, 45-50% EtOAc/Hexane) gave 35-3 as a white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additionresidue was diluted with EtOAc
  3. washwashed with water (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3a2acc7cde54fb1ad65776877f717c9
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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