Dichloromethane → HCID 178462115, compound

HRID 1944714Notes

Reaction equation

HRID 1944714 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14][CH2:13]2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)[Cl:27]>C(O)(C(F)(F)F)=O>[ClH:27].[NH2:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([C:10]([NH:9][C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:8])=[O:11])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 178462117HCID 178462117, compound2×

Product 1

HCID 178462115HCID 178462115, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl trans-4-((R)-1-phenylethylcarbamoyl)cyclohexylcarbamate (Intermediate 41, 5.2 g) was dissolved in DCM (50 mL) to which TFA was added. The resulting mixture was stirred for 45 min at room temperature. LC-MS of material showed one major peak which corresponded to desired product. The reaction mixture was then concentrated to give a clear oil. The oil was then dissolved in diethyl ether (200 mL) to which HCl (2M solution in ether) (20 mL) was added. The resulting mixture was stirred at room temperature for 2 h, resulting in a white precipitate that was collected by filtration and washed with diethyl ether (4.1 g).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-60809547d0314ba799d54b8e32f7cf84
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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