Ethanol → tert-butyl (2S,3S)-2-[3-({2-[(isopropylamino)methyl]-1,3-thiazol-4-yl}methyl)-2-oxo-1-imidazolidinyl]-3-methylpentanoate

HRID 243604Notes

Reaction equation

HRID 243604 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[C:6]([CH2:8][N:9]2[CH2:13][CH2:12][N:11]([C@@H:14]([CH:22]([CH3:24])[CH3:23])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]2=[O:25])[N:7]=1)=O.[CH2:26](O)C.[CH:29]([NH2:32])([CH3:31])[CH3:30].[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH:29]([NH:32][CH2:1][C:3]1[S:4][CH:5]=[C:6]([CH2:8][N:9]2[CH2:13][CH2:12][N:11]([C@@H:14]([C@@H:22]([CH3:24])[CH2:23][CH3:26])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]2=[O:25])[N:7]=1)([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 702EthanolHCID 6363IsopropylamineHCID 4311764Sodium borohydrideHCID 87193539Tert-butyl(2s)-2-{3-[(2-formyl-1,3-thiazol-4-yl)methyl]-2-oxo-1-imidazolidinyl}-3-methylbutanoate

Product 1

HCID 66889849tert-butyl (2S,3S)-2-[3-({2-[(isopropylamino)methyl]-1,3-thiazol-4-yl}methyl)-2-oxo-1-imidazolidinyl]-3-methylpentanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of Example 273D (65 mg) in toluene:ethanol (0.7 mL, 1:1) was treated with isopropylamine (0.14 mL, 10 equivalents), stirred at 70° C. in a capped vial for 2 hrs. The mixture was cooled to 25° C. and NaBH4 (19 mg, 3 equivalents) was added and the mixture was stirred at 25° C. for 3 days. The solvents were evaporated, and the residue was partitioned between ethyl acetate and saturated NaHCO3, the organic layer was separated and washed with brine, dried over MgSO4, filtered and evaporated to give 59 mg of the title compound.

Workup

  1. temperatureThe mixture was cooled to 25° C.
  2. stirringthe mixture was stirred at 25° C. for 3 days
  3. customThe solvents were evaporated
  4. customthe residue was partitioned between ethyl acetate and saturated NaHCO3
  5. customthe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-a8b0c0cdfca04f38bb02fd2e48057475
Source dataset
uspto-grants-2014_02
Patent number
US08653141B2

Reaction notes

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