Hydrochloric Acid → HCID 57918994, compound

HRID 2266293Notes

Reaction equation

HRID 2266293 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C@@H:4]([OH:13])[CH2:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7].[CH3:21][C:22]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])[CH3:23].N1C=CN=C1>CN(C=O)C.CCOC(C)=O>[NH2:2][C@@H:3]([CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C@@H:4]([O:13][Si:25]([C:22]([CH3:24])([CH3:23])[CH3:21])([CH3:27])[CH3:26])[CH2:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57918884HCID 57918884, compound

Product 1

HCID 57918994HCID 57918994, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the HCl salt of (3S,4S)-4-amino-N-butyl-5-cyclohexyl-3-hydroxypentanamide (279 mg, 1.03 mmol), TBSCl (311 mg, 2.06 mmol) and imidazole (281 mg, 4.12 mmol) in dry DMF (2 mL) was stirred at rt for 2 d. The mixture was diluted with EtOAc (90 mL), washed with 1:1 water/brine (3×20 mL), dried over Na2SO4 and concentrated to leave crude (3S,4S)-4-amino-N-butyl-3-(tertbutyldimethylsilyloxy)-5-cyclohexylpentanamide (311 mg, 78%) as a yellow syrup.

Workup

  1. washwashed with 1:1 water/brine (3×20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5d702ebe96ba4ac29de2d639d416dfa8
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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