Chlorosuccinimide → HCID 68349037, compound

HRID 1961326Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:9][C@@H:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:8])[S:5][CH:6]=1.N[C@@H](CC1C=CC([Cl:48])=CC=1Cl)CN1C(=O)C2C(=CC=CC=2)C1=O.C1C(=O)N(Cl)C(=O)C1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:9][C@@H:10]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:8])[S:5][C:6]=1[Cl:48]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 1,1-dimethylethyl ((2S)-2-{[(4-bromo-2-thienyl)carbonyl]amino}-3-phenylpropyl)carbamate (prepared according to Preparation 22), except substituting 2-[(2S)-2-amino-3-phenylpropyl]-1H-isoindole-1,3(2H)-dione for 2-[(2S)-2-amino-3-(2,4-dichlorophenyl)propyl]-1H-isoindole-1,3(2H)-dione (200 mg, 0.455 mmol) and NCS (61 mg, 0.455 mmol) in DMF (3 ml) was heated at 50° C. in a sealed tube for 2 hours. The solvent was removed and the residue was purified by biotage (30% Hex/EtOAc) to give the title product (140 mg, 65%).

Workup

customThe solvent was removed
customthe residue was purified by biotage (30% Hex/EtOAc)

Sources & evidence

ORD record: ord-250b0b6cb9a1441d862e89f8a9f69952
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410158B2

Reaction notes

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