Dichloromethane → (2S,4R)-2-amino-4-ethoxy-pentanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide hydrochloride

HRID 19039Notes

Reaction equation

HRID 19039 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:15](=[O:27])[NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[N:18]=1)[CH2:9][C@H:10]([O:12][CH2:13][CH3:14])[CH3:11])(C)(C)C.FC(F)(F)C(O)=O.[Cl:36]CCl>>[ClH:36].[OH:26][C:23]([CH3:25])([CH3:24])[CH2:22][N:19]1[CH:20]=[CH:21][C:17]([NH:16][C:15](=[O:27])[C@@H:8]([NH2:7])[CH2:9][C@H:10]([O:12][CH2:13][CH3:14])[CH3:11])=[N:18]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66899703{(1S,3R)-3-ethoxy-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-butyl}-carbamic acid t-butyl ester

Product 1

HCID 66898549(2S,4R)-2-amino-4-ethoxy-pentanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide hydrochloride

Procedure

To a solution of {(1S,3R)-3-ethoxy-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-butyl}-carbamic acid t-butyl ester (306 mg) in dichloromethane (3 mL) was added trifluoroacetic acid (2 mL). The solution was stirred at room temperature for 30 min. Solvents were evaporated and the residue was dried in vacuo. The resulting waxy material was dissolved in methanolic hydrogen chloride solution (5 mL). Solvents were evaporated and the residue was dried in vacuo. The white solid was triturated with dry diethyl ether and filtered to afford (2S,4R)-2-amino-4-ethoxy-pentanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide hydrochloride (274 mg). For the neutral free amine, LR-ES-MS m/z calculated for C14H26N4O3 [M]+298, observed [M+H]+ 299.

Workup

  1. customSolvents were evaporated
  2. customthe residue was dried in vacuo
  3. dissolutionThe resulting waxy material was dissolved in methanolic hydrogen chloride solution (5 mL)
  4. customSolvents were evaporated
  5. customthe residue was dried in vacuo
  6. customThe white solid was triturated with dry diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-0c0b2ce79c9a41829a202a422f29b6f1
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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