Acetic Acid → HCID 67235406, compound

HRID 1521692Notes

Reaction equation

HRID 1521692 reaction equation
[C:1]([O:5][C:6]([N:8]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:9][CH2:10][C:11]([NH:14][C:15]1[CH:16]=[C:17]([CH:28]=[CH:29][C:30]=1[N+:31]([O-])=O)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>CO.[Zn]>[NH2:31][C:30]1[CH:29]=[CH:28][C:17]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])=[CH:16][C:15]=1[NH:14][C:11]([CH3:13])([CH2:10][CH2:9][N:8]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH3:12]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67235192HCID 67235192, compound

Product 1

HCID 67235406HCID 67235406, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred suspension of benzyl 3-({4-[bis(tert-butoxycarbonyl)amino]-2-methylbutan-2-yl}amino)-4-nitrobenzoate (280 mg, 0.50 mmol) and zinc dust (344 mg, 5.27 mmol) in methanol (9 mL) is added acetic acid (0.34 mL), dropwise. The mixture is stirred for 20 min, methanol (50 mL) is added and the mixture is filtered through Celite. The filtrate is concentrated and partitioned between EtOAc and H2O, adjusting the pH to 5 by adding 1M HCl. The organic layer is washed with NaHCO3 and H2O, dried (MgSO4) and evaporated to afford the title compound (250 mg, 94%) which is used in the next step without further purification.

Workup

  1. filtrationthe mixture is filtered through Celite
  2. concentrationThe filtrate is concentrated
  3. custompartitioned between EtOAc and H2O
  4. additionby adding 1M HCl
  5. washThe organic layer is washed with NaHCO3 and H2O
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-206f2eb1ef6646719ca870a4e1da84cb
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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