Ethyl chloroformate → HCID 86595603, compound

HRID 1246503Notes

Reaction equation

HRID 1246503 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>[C:18]([O:17][C:16]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:35](=[O:36])[O:37][CH2:38][CH3:39])[S:3][C:4]=2[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[CH:14][CH:13]=1)=[O:22])([CH3:21])([CH3:20])[CH3:19]

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-ec392dbcf67a4df5b51fcb6f972a7b9b
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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