Lithium borohydride → Tert-butyl 2-{[4-(hydroxymethyl)benzoyl]amino}-4-thien-2-ylphenylcarbamate

HRID 1919884Notes

Reaction equation

HRID 1919884 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27](OC)=[O:28])=[CH:25][CH:24]=1)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1>[OH:28][CH2:27][C:26]1[CH:31]=[CH:32][C:23]([C:21]([NH:20][C:10]2[CH:11]=[C:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[CH:13]=[CH:14][C:9]=2[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:22])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57607810Methyl 4-[({2-[(tert-butoxycarbonyl)amino]-5-thien-2-ylphenyl}amino)carbonyl]benzoate

Product 1

HCID 57607813Tert-butyl 2-{[4-(hydroxymethyl)benzoyl]amino}-4-thien-2-ylphenylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 4-[({2-[(tert-butoxycarbonyl)amino]-5-thien-2-ylphenyl}amino)carbonyl]benzoate (1.7 g, 3.76 mmol) was made 0.1 M in anhydrous THF and cooled to 0° C. To this stirring suspension was added LiBH4 (0.55 g, 25.20 mmol), 2M in anhydrous THF. The resulting solution was slowly warmed to ambient temperature stirred for 14 hours. The reaction was then cooled to 0° C. and carefully quenched with saturated aqueous NH4Cl. The mixture was diluted with water and extracted with ethyl acetate two times. The combined organic layers were washed with brine then dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was diluted with DCM and purified by MPLC to give tert-butyl 2-{[4-(hydroxymethyl)benzoyl]amino}-4-thien-2-ylphenylcarbamate.

Workup

  1. temperatureThe resulting solution was slowly warmed to ambient temperature
  2. temperatureThe reaction was then cooled to 0° C.
  3. customcarefully quenched with saturated aqueous NH4Cl
  4. additionThe mixture was diluted with water
  5. extractionextracted with ethyl acetate two times
  6. washThe combined organic layers were washed with brine
  7. dry with materialthen dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. additionThe residue was diluted with DCM
  10. custompurified by MPLC

Sources & evidence

ORD record
ord-c13a7ce2c5b24675aa61573d292fd0f1
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

Loading…