Hydrochloric Acid → (3aS,5S,6aR)-5-amino-N-(2-hydroxy-5-(trifluoromethyl)benzyl)hexahydro-2H-cyclopenta[b]furan-3a-carboxamide dihydrochloride

HRID 1747152Notes

Reaction equation

HRID 1747152 reaction equation
C([O:5][C:6]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:7]=1[CH2:8][NH:9][C:10]([C@:12]12[CH2:19][C@H:18]([NH:20]C(=O)OC(C)(C)C)[CH2:17][C@H:13]1[O:14][CH2:15][CH2:16]2)=[O:11])(C)(C)C.[ClH:36]>CO>[ClH:36].[ClH:36].[NH2:20][C@@H:18]1[CH2:17][C@H:13]2[O:14][CH2:15][CH2:16][C@@:12]2([C:10]([NH:9][CH2:8][C:7]2[CH:28]=[C:29]([C:32]([F:33])([F:34])[F:35])[CH:30]=[CH:31][C:6]=2[OH:5])=[O:11])[CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86708153tert-butyl ((3aS,5S,6aR)-3a-((2-(tert-butoxy)-5-(trifluoromethyl)benzyl)carbamoyl)hexahydro-2H-cyclopenta[b]furan-5-yl)carbamate

Product 1

HCID 86708151(3aS,5S,6aR)-5-amino-N-(2-hydroxy-5-(trifluoromethyl)benzyl)hexahydro-2H-cyclopenta[b]furan-3a-carboxamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of the product of Step A (11.07 g, 20.57 mmol, 1 eq) in methanol (60 mL) and solution of HCl in methanol (82 mL of 1.25 M solution, 103 mmol, 5 eq) was heated to 55° C. for 2.5 days. The solution was concentrated to give the product of step B. Calculated for C16H19F3N2O3: 345.1 (M+1). found: 345.3.

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-c688a88b8ad04576bd2ab6f45b4c552f
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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