Water → HCID 178525088, compound

HRID 1268966Notes

Reaction equation

HRID 1268966 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[NH2:8][C@@H:9]([CH2:20][CH2:21][C:22]1[NH:23][CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:26]=1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O>O1CCCC1.C(OCC)(=O)C>[C:27]1([C:25]2[N:26]=[C:22]([CH2:21][CH2:20][C@H:9]([NH:8][CH2:6][C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)[C:10]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[NH:23][CH:24]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 962WaterHCID 681353-ThiophenecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178511818HCID 178511818, compound

Product 1

HCID 178525088HCID 178525088, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Thiophene-3-carboxaldehyde (1 ml; 1 eq.) is added to a solution of benzyl (2S)-2-amino-4-(4-phenyl-1H-imidazol-2-yl)butanoate in the form of a free base (3.6 g; 1 eq.) in tetrahydrofuran (hereafter THF, 40 ml). The mixture is stirred for 15 hours at approximately 20° C. and diluted by adding 50 ml of tetrahydrofuran. NaBH(OAc)3 (4.73 g; 2 eq.) is then added. After 1 hour of stirring at approximately 20° C., the reaction is stopped by adding water (40 ml) and ethyl acetate is then added (100 ml). After decantation and extraction, the combined organic phases are washed with salt water, dried over Na2SO4 then evaporated under reduced pressure at 40° C. Flash chromatography purification on silica gel (eluent: ethyl acetate/heptane 9:1) yields the expected compound in the form of a yellow oil (3.08 g; 66% yield).

Workup

  1. additiondiluted
  2. stirringAfter 1 hour of stirring at approximately 20° C.
  3. additionis then added (100 ml)
  4. extractionAfter decantation and extraction
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. customthen evaporated under reduced pressure at 40° C
  8. customFlash chromatography purification on silica gel (eluent: ethyl acetate/heptane 9:1)

Sources & evidence

ORD record
ord-66afce8a699c4773a48caa1a325b9fa5
Source dataset
uspto-grants-2007_04
Patent number
US07199145B2

Reaction notes

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