Acetic Acid → HCID 53629881, compound

HRID 1642181Notes

Reaction equation

HRID 1642181 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12][C:11]=2[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.N>C1(C)C=CC=CC=1>[C:1]1([C@@H:7]([NH:9][C@H:10]2[C@@H:11]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:12][CH2:13][N:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:15]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 5049666Sodium triacetoxyborohydrideHCID 16099060HCID 16099060, compound

Product 1

HCID 53629881HCID 53629881, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product of Example 61A (62.3 g, 0.167 mol), NaBH(OAc)3 (150.0 g, 0.708 mol), and powdered 4 Å molecular sieves (133.0 g) in toluene (730 mL) in a 3-neck round bottom flask equipped with a mechanical stirrer, thermometer and addition funnel at 0° C. was treated with acetic acid (191 mL, 3.30 mol) dropwise. After the addition was complete, the ice-bath was removed and the mixture was stirred for 20 hours, filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in ethyl acetate (1000 mL) and quenched by slow addition of saturated aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure to provide the product as a ˜1:1.5 mixture of the two (cis) isomers (60.0 g, 0.159 mol, 94% yield). MS (DCI/NH3) m/z 377 (M+H)+.

Workup

  1. customequipped with a mechanical stirrer
  2. additionthermometer and addition funnel at 0° C.
  3. additionAfter the addition
  4. customthe ice-bath was removed
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate (1000 mL)
  8. customquenched by slow addition of saturated aqueous NaHCO3
  9. customThe layers were separated
  10. extractionthe aqueous layer was extracted with ethyl acetate
  11. dry with materialThe combined organics were dried over Na2SO4
  12. filtrationfiltered
  13. concentrationthe filtrate concentrated under reduced pressure
  14. customto provide the product
  15. additionas a ˜1:1.5 mixture of the two (cis) isomers (60.0 g, 0.159 mol, 94% yield)

Sources & evidence

ORD record
ord-ec8d616c9bce4a7290e63a6c458d510f
Source dataset
uspto-grants-2012_02
Patent number
US08119635B2

Reaction notes

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