1,2-Dichloroethane → 3-Oxo-2-[2-(pyrimidin-2-ylamino)ethyl]-2,3-dihydro-1H-isoindole-5-carbonyl-2(S)phenylsulfonylamino-beta-alanine t-butyl ester

HRID 582690

Reaction equation

HRID 582690 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11](O)=[O:12])[CH:9]=2)[CH2:4][N:3]1[CH2:14][CH2:15][NH:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.Cl.[NH2:24][CH2:25][C@H:26]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:30]([O:29][C:27](=[O:28])[C@@H:26]([NH:34][S:35]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)(=[O:37])=[O:36])[CH2:25][NH:24][C:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH2:4][N:3]([CH2:14][CH2:15][NH:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[C:2]2=[O:1])=[O:12])([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochlorideHCID 701036023-Oxo-2-[2-(pyrimidin-2-ylamino)ethyl]-2,3-dihydro-1H-isoindole-5-carboylic acid

Product 1

HCID 1317213113-Oxo-2-[2-(pyrimidin-2-ylamino)ethyl]-2,3-dihydro-1H-isoindole-5-carbonyl-2(S)phenylsulfonylamino-beta-alanine t-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A DMF solution (10 mL) of acid 6-4 (382 mg, 1.28 mmol) 1-4 (517 mg, 1.54 mmol), HOBT (264 mg, 1.13 mmol) NMM (563 μl, 5.1 mmol) and EDC (331 mg, 1.73 mmol) was stirred under ambient conditions for 18 h. The DMF was removed at 50° C. and the residue partitioned between EtOAc and H2O. The organic layer was washed with sat. NaHCO3 solution, brine, and dried (MgSO4). Evaporation gave a yellow foam which was purified by flash chromatography (silica, 3:1 acetone/CH2Cl2) to provide 6-5 as a colorless foam.

Workup

  1. customThe DMF was removed at 50° C.
  2. customthe residue partitioned between EtOAc and H2O
  3. washThe organic layer was washed with sat. NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation
  6. customgave a yellow foam which
  7. customwas purified by flash chromatography (silica, 3:1 acetone/CH2Cl2)

Sources & evidence

ORD record
ord-01aea64beafc40a39d741df03c0dd7a8
Source dataset
uspto-grants-1999_07
Patent number
US05925655

Linked notes

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