tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)cyclohexylcarbamate → HCID 86618149, compound

HRID 2246579Notes

Reaction equation

HRID 2246579 reaction equation
[C:1]([NH:4][C@H:5]1[C@@H:10]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16]C(OCC3C=CC=CC=3)=O)[C:12]2=[O:27])[CH2:9][CH2:8][C@@H:7]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:6]1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([NH:4][C@H:5]1[C@@H:10]([N:11]2[CH2:15][CH2:14][C@H:13]([NH2:16])[C:12]2=[O:27])[CH2:9][CH2:8][C@@H:7]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86618124tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)cyclohexylcarbamate

Product 1

HCID 86618149HCID 86618149, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)cyclohexylcarbamate (1.7 g, 3.48 mmol; see Example 1, Step 6) in methanol (10 mL) was added 10% Pd/C (0.6 g of 50% wet catalyst). The flask was evacuated and back-filled with hydrogen with a hydrogen balloon. The mixture was stirred at room temperature under 1 atm of hydrogen for 14 h and the catalyst was removed by filtration. The filtrate was concentrated in vacuo to provide tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-3-amino-2-oxopyrrolidin-1-yl)cyclohexylcarbamate, which was taken on to the next step without further purification. LC/MS found [M+H]+=355.

Workup

  1. customThe flask was evacuated
  2. additionback-filled with hydrogen with a hydrogen balloon
  3. customthe catalyst was removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3e8c75a596014662bbca3b0d44c71a6c
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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