Acetic Acid → HCID 67969538, compound

HRID 1746374Notes

Reaction equation

HRID 1746374 reaction equation
CC(O)=O.[C:5]([O:9][C:10](=[O:38])[NH:11][C@H:12]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)[C:13]([CH:15]1[C:20](=[O:21])[O:19][C:18]([CH3:23])([CH3:22])[O:17][C:16]1=[O:24])=O)([CH3:8])([CH3:7])[CH3:6].[BH4-].[Na+].[Na+].[Cl-]>CC#N.O>[C:5]([O:9][C:10](=[O:38])[NH:11][C@@H:12]([CH2:13][CH:15]1[C:20](=[O:21])[O:19][C:18]([CH3:23])([CH3:22])[O:17][C:16]1=[O:24])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:30][CH:31]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 5234Sodium Chloride2×HCID 4311764Sodium borohydrideHCID 67986785HCID 67986785, compound

Product 1

HCID 67969538HCID 67969538, compoundYield 17.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
-5 °C

Procedure

AcOH (8.6 mL) was added to a solution of crude [(R)-1-biphenyl-4-ylmethyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid t-butyl ester (6.4 g, 14 mmol) in anhydrous MeCN (90 mL) was added AcOH (8.6 mL) at −5° C. under nitrogen. The mixture was stirred at −5° C. for 30 minutes, then sodium borohydride (1.3 g, 34.5 mmol) was added in small portions over 2 hours. After stirring for another 1 hour at −5° C., saturated aqueous NaCl and 1.7 M of NaCl in water (30 mL) was added. The layers were separated and the organic layer was washed with saturated aqueous NaCl (2×30 mL) and water (2×30 mL), dried under MgSO4, filtered and evaporated. The resulting crude product was further purified by chromatography (5:1 heptane:EtOAc) to yield [(S)-2-biphenyl-4-yl-1-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)ethyl]carbamic acid t-butyl ester (1.1 g, purity 98.4%) as a light yellow solid.

Workup

  1. stirringAfter stirring for another 1 hour at −5° C.
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated aqueous NaCl (2×30 mL) and water (2×30 mL)
  4. customdried under MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting crude product was further purified by chromatography (5:1 heptane:EtOAc)

Sources & evidence

ORD record
ord-347c1fe66720464199717ecc1998c95a
Source dataset
uspto-grants-2015_10
Patent number
US09150500B2

Reaction notes

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