tert-Butanol → HCID 59536878, compound

HRID 220671Notes

Reaction equation

HRID 220671 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].Cl[S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8].[NH2:13][CH2:14][CH:15]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1.C(N(CC)C(C)C)(C)C>ClCCl>[C:29]([O:28][C:27]([NH:26][CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)[CH2:14][NH:13][S:7]([NH:10][C:11](=[O:12])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:9])=[O:8])=[O:33])([CH3:30])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanateHCID 81531DiisopropylethylamineHCID 43094068tert-butyl N-{2-amino-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Product 1

HCID 59536878HCID 59536878, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 110 mg (1.48 mmol) of tert-butanol in 2 ml of dichloromethane was cooled to 0° C. and admixed dropwise with a solution of 129 μl (1.48 mmol) of chlorosulphonyl isocyanate in 2 ml of dichloromethane. The mixture was stirred at RT for 1 h. In a syringe, 820 μl of this solution were taken and were added dropwise to a solution of 90 mg (296 μmol) of the compound from Example 22A in 2 ml of dichloromethane. Then 103 μl of N,N-diisopropylethylamine were added and the reaction mixture was stirred further at RT for 2 h. The volatile constituents were removed on a rotary evaporator. The residue was dissolved in a little acetonitrile and admixed with 1 ml of 1M hydrochloric acid, and the solution obtained was purified by preparative HPLC [Method 23]. The product-containing fraction was freed from the solvents on a rotary evaporator and the residue was dried in an HV. This gave 111 mg (76% of theory) of the title compound.

Workup

  1. stirringthe reaction mixture was stirred further at RT for 2 h
  2. customThe volatile constituents were removed on a rotary evaporator
  3. dissolutionThe residue was dissolved in a little acetonitrile
  4. customthe solution obtained
  5. customwas purified by preparative HPLC [Method 23]
  6. customThe product-containing fraction was freed from the solvents on a rotary evaporator
  7. customthe residue was dried in an HV

Sources & evidence

ORD record
ord-393b5c1cd4624f1bb5e6a05d32ca599d
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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