3,4-Dichlorophenyl isocyanate → HCID 67151622, compound

HRID 1805221Notes

Reaction equation

HRID 1805221 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[Cl:33][C:34]1[CH:35]=[C:36]([N:41]=[C:42]=[O:43])[CH:37]=[CH:38][C:39]=1[Cl:40]>ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:42]([NH:41][C:36]3[CH:37]=[CH:38][C:39]([Cl:40])=[C:34]([Cl:33])[CH:35]=3)=[O:43])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 76073,4-Dichlorophenyl isocyanateHCID 81531DiisopropylethylamineHCID 66705807HCID 66705807, compound

Product 1

HCID 67151622HCID 67151622, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of (S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (180 mg) in dichloromethane (3 ml) were added sequentially N,N-diisopropylethylamine (0.19 ml) and 3,4-dichlorophenyl isocyanate (137 mg, CAS 102-36-3) and stirring was continued at room temperature for 18 h. The mixture was then concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S)-4-(2-{4-[3-(3,4-dichloro-phenyl)-ureido]-phenyl}-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (267 mg, 93%) as a colourless amorphous solid. MS (ISP): 529.4 ([{37Cl}M+NH4]+), 527.4 ([{37Cl35Cl}M+NH4]+), 525.4 ([{35Cl}M+NH4]+), 512.2 ([{37Cl}M+H]+), 510.2 ([{37Cl35Cl}M+H]+), 508.2 ([{35Cl}M+H]+), 456.2 ([{37Cl}M+H—C4H8]+), 454.2 ([{37Cl35Cl}M+H—C4H8]+), 452.2 ([{35Cl}M+H—C4H8]+).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

Sources & evidence

ORD record
ord-89241a6103a34b27b754d5cf7f7eba38
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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