Ethyl chloroformate → HCID 86595603, compound

HRID 2117913Notes

Reaction equation

HRID 2117913 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[C:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=2)[N:6]=1.Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36]>N1C=CC=CC=1>[CH2:38]([O:37][C:35](=[O:36])[NH:1][C:2]1[S:3][C:4]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[C:5]([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])=[CH:13][CH:14]=2)[N:6]=1)[CH3:39]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 86595602HCID 86595602, compound

Product 1

HCID 86595603HCID 86595603, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl [4-(2-{2-amino-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]carbamate (140 mg) was dissolved in pyridine (2 ml) under N2 atmosphere. Then, ethyl chloroformate (30.2 ml) was added to the solution at 0° C. The reaction mixture was stirred at r.t. for 2 hours, and concentrated in vacuo. The residue was dissolved in AcOEt, and washed with 1N—HCl, water and brine. The organic layer was dried over anhydrous MgSO4, and concentrated in vacuo to give ethyl{4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}carbamate (155.8 mg) as an off-white amorphous substance.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in AcOEt
  3. washwashed with 1N—HCl, water and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bb355fb857b4ef38840f0434c4861d2
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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