Hydrochloric Acid → 3-Amino-N-cyclopropyl-2-hydroxy-4-phenylbutanamide Hydrochloride

HRID 882853Notes

Reaction equation

HRID 882853 reaction equation
[ClH:1].[CH:2]1([NH:5][C:6](=[O:25])[CH:7]([OH:24])[CH:8]([NH:16]C(=O)OC(C)(C)C)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.COC(C)(C)C>C(Cl)Cl>[ClH:1].[NH2:16][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:7]([OH:24])[C:6]([NH:5][CH:2]1[CH2:4][CH2:3]1)=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 15413tert-Butyl methyl etherHCID 66645006Tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamate

Product 1

HCID 666450253-Amino-N-cyclopropyl-2-hydroxy-4-phenylbutanamide HydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl (4 M in dioxane, 16 mL, 64.00 mmol) was added dropwise to a solution of tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamate (7.5 g, 22.43 mmol) in DCM (130 mL). After stirring for 5 h additional HCl (4 M in dioxane, 5 mL, 20.00 mmol) was added and the stirring was continued overnight. The solvent was reduced in vacuo and methyl-tert-butyl-ether (200 mL) was added. The precipitate obtained was filtered, washed with methyl-tert-butyl-ether and n-pentane and dried providing the title compound (5.8 g, 96%).

Workup

  1. additionwas added
  2. additionwas added
  3. customThe precipitate obtained
  4. filtrationwas filtered
  5. washwashed with methyl-tert-butyl-ether and n-pentane
  6. customdried

Sources & evidence

ORD record
ord-b82b41cc4fa94743a6c85fe637d39ccd
Source dataset
uspto-grants-2012_08
Patent number
US08236798B2

Reaction notes

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