Acetic Anhydride → (S)-4-tert-butoxycarbonylamino-4-[4-(N-acetylhydroxycarbamimidoyl)-benzyl carbamoyl]-butyric acid benzyl ester

HRID 2404001Notes

Reaction equation

HRID 2404001 reaction equation
[CH2:1]([O:8][C:9](=[O:35])[CH2:10][CH2:11][C@H:12]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:13](=[O:26])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[NH:25])[NH:23][OH:24])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(O)(=O)C>[CH2:1]([O:8][C:9](=[O:35])[CH2:10][CH2:11][C@H:12]([NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:13](=[O:26])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[NH:25])[N:23]([OH:24])[C:36](=[O:38])[CH3:37])=[CH:18][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178454209(S)-4-tert-butoxycarbonylamino-4-[4-(N-hydroxycarbamimidoyl)-benzyl carbamoyl]-butyric acid benzyl ester

Product 1

HCID 86658625(S)-4-tert-butoxycarbonylamino-4-[4-(N-acetylhydroxycarbamimidoyl)-benzyl carbamoyl]-butyric acid benzyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of compound II (14.8 g, 20.0 mmol) and acetic anhydride (5.7 ml, 60.0 mmol) in acetic acid (100 ml) was stirred at room temperature for 45 min, and then solvent was evaporated in vacuo. The resultant residue was dissolved in EtOAc (300 ml) and extracted with water (2×75 ml) and brine (75 ml). The organic layer was then dried over MgSO4, evaporated and dried in vacuo to provide compound JJ (9.58 g, 18.2 mmol) as yellowish solid. LC-MS [M+H] 527.6 (C27H34N4O7+H, calc: 527.9). Compound JJ was used without further purification.

Workup

  1. customsolvent was evaporated in vacuo
  2. dissolutionThe resultant residue was dissolved in EtOAc (300 ml)
  3. extractionextracted with water (2×75 ml) and brine (75 ml)
  4. dry with materialThe organic layer was then dried over MgSO4
  5. customevaporated
  6. customdried in vacuo
  7. customto provide compound JJ (9.58 g, 18.2 mmol) as yellowish solid
  8. customCompound JJ was used without further purification

Sources & evidence

ORD record
ord-da18caf77f1b47ae86a5c69dbb31a177
Source dataset
uspto-grants-2014_08
Patent number
US08802681B2

Reaction notes

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