Water → benzyl (S)-1-((1S,2R,4R)-2-formamido-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

HRID 2246589Notes

Reaction equation

HRID 2246589 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C@H:6]([N:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[CH2:5][CH2:4][C@@H:3]1[N:13]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14]1=[O:29].[CH2:30](N(CC)CC)C.[OH2:37]>ClCCl>[CH:30]([NH:1][C@@H:2]1[CH2:7][C@H:6]([N:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[CH2:5][CH2:4][C@@H:3]1[N:13]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:14]1=[O:29])=[O:37]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 86618151benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

Product 1

HCID 86618152benzyl (S)-1-((1S,2R,4R)-2-formamido-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 460 mg (10 mmol) of formic acid, acetic anhydride (204 mg, 2 mmol) was added. The mixture was stirred at room temperature for 2 h. Then one fifth of the above solution was added to a mixture of benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (60 mg, 0.149 mmol) in dichloromethane (3 ml) and triethylamine (62.3 μl, 3 eq) at 0° C. with stirring. The reaction was stirred for 1 h at room temperature and 1 ml of water was added to quench the reaction. The mixture was diluted with dichloromethane (60 ml) and washed with saturated NaHCO3 (20 ml). The solution was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give benzyl (S)-1-((1S,2R,4R)-2-formamido-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (50 mg, 78%). LC/MS found [M+H]+=431.

Workup

  1. stirringwith stirring
  2. stirringThe reaction was stirred for 1 h at room temperature
  3. customto quench
  4. customthe reaction
  5. washwashed with saturated NaHCO3 (20 ml)
  6. dry with materialThe solution was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8409d00ba3114311a29d898a088087a4
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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