HCID 57918949, compound → HCID 57918884, compound

HRID 2266292Notes

Reaction equation

HRID 2266292 reaction equation
[CH2:1]([NH:5][C:6](=[O:26])[CH2:7][C@H:8]([OH:25])[C@@H:9]([NH:17]C(=O)OC(C)(C)C)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:2][CH2:3][CH3:4]>Cl.O1CCOCC1>[NH2:17][C@@H:9]([CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[C@@H:8]([OH:25])[CH2:7][C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:26]

Participants

4

Reactant 1

HCID 57918949HCID 57918949, compound

Product 1

HCID 57918884HCID 57918884, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl (2S,3S)-5-(butylamino)-1-cyclohexyl-3-hydroxy-5-oxopentan-2-ylcarbamate (394 mg, 1.1 mmol) was dissolved in 4M HCl in dioxane (5 mL, 200 mmol and stirred at rt for 4 h. Removal of the solvent left a sticky solid (344 mg). This material was taken up in 10% aq K2CO3 (20 mL) and extracted with CH2Cl2 (4×30 mL). The combined CH2Cl2 extracts were dried over MgSO4 and concentrated to afford (3S,4S)-4-Amino-N-butyl-5-cyclohexyl-3-hydroxypentanamide (279 mg, 97%).

Workup

  1. customRemoval of the solvent
  2. waitleft a sticky solid (344 mg)
  3. extractionextracted with CH2Cl2 (4×30 mL)
  4. dry with materialThe combined CH2Cl2 extracts were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-87961f5170fe43d6a04843e94a5e97b6
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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