HCID 86690075, compound → HCID 86599587, compound

HRID 520354Notes

Reaction equation

HRID 520354 reaction equation
[C:1]([O:4][CH2:5][C:6]([CH3:27])([CH3:26])[C@H:7]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:8]([O:10]CC1C=CC=CC=1)=[O:9])(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][CH2:5][C:6]([CH3:27])([CH3:26])[C@H:7]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86690075HCID 86690075, compound

Product 1

HCID 86599587HCID 86599587, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-benzyl 4-acetoxy-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoate (0.26 g) in MeOH (10 mL) was added 10% Pd/C (0.020 g) under N2. The reaction mixture was stirred under H2 at rt for 16 h. The reaction was filtered through diatomaceous earth (Celite®), washed with EtOAc and concentrated to yield (S)-4-acetoxy-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (0.18 g). LC/MS (Cond. N-1): [M+Na]+ 312.21, RT=3.12 min.

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth (Celite®)
  2. washwashed with EtOAc
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6c70b3e18d9e4f419cb381862b4fa3e2
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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