Acetic Anhydride → HCID 54414235, compound

HRID 2296671Notes

Reaction equation

HRID 2296671 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH2:9][CH2:10][S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:16]([C:27]([NH:29][O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:28])[CH2:15]1)(=[O:13])=[O:12]>CC(O)=O>[C:1]([NH:8][CH2:9][CH2:10][S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:16]([C:27]([NH:29][O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:28])[CH2:15]1)(=[O:13])=[O:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54417248HCID 54417248, compound

Product 1

HCID 54414235HCID 54414235, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic anhydride (36 mg) was added to a solution of (2R)-4-(2-aminoethanesulfonyl)-N-tert-butoxy-1-tert-butoxycarbonyl-2-piperazinecarboxamide (130 mg) in AcOH (2 ml). The reaction mixture was stirred at ambient temperature for 3 hours. The mixture was concentrated in vacuo, and the residue was partitioned between AcOEt and saturated aqueous NaHCO3 solution. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated in vacuo to give 142 mg of (2R)-4-[2-(acetylamino)-ethanesulfonyl]-N-tert-butoxy-1-tert-butoxycarbonyl-2-piperazinecarboxamide.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between AcOEt and saturated aqueous NaHCO3 solution
  3. washThe organic layer was washed with saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c65dc1804e4b4a69b115274325ec3f14
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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