Acetic Anhydride → HCID 67443497, compound

HRID 2403990Notes

Reaction equation

HRID 2403990 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH2:30])[C:13](=[O:29])[NH:14][CH2:15][CH2:16][N:17]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH3:18])([CH3:4])([CH3:3])C.CCN(C(C)C)C(C)C.[CH3:41][C:42](OC(C)=O)=[O:43]>C(Cl)(Cl)Cl>[CH:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:30][C:42](=[O:43])[CH3:41])[C:13](=[O:29])[NH:14][CH2:15][CH2:16][N:17]([C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[CH3:18])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 66994670HCID 66994670, compound

Product 1

HCID 67443497HCID 67443497, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of compound H (1.4 g, 3.21 mmol) in CHCl3 (10 mL) at room temperature was added DIEA (2.6 mL, 15 mmol) followed by Ac2O (0.85 mL, 9.0 mmol). The reaction mixture was stirred at room temperature for 2 h. Solvents were removed in vacuo and then the residue was dissolved in dichloromethane (100 mL). The organic layer was washed with 10% citric acid (75 mL), saturated NaHCO3 (75 mL) and brine (75 mL). The organic layer was separated, dried over Na2SO4 and solvent removed in vacuo to afford compound I (1.45 g, 99%). LC-MS [M+H] 479.5 (C24H38N4O6+H, calc: 479.5).

Workup

  1. customSolvents were removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (100 mL)
  3. washThe organic layer was washed with 10% citric acid (75 mL), saturated NaHCO3 (75 mL) and brine (75 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4 and solvent
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-55e5ec28dae94889aaac9ed1232e0847
Source dataset
uspto-grants-2014_08
Patent number
US08802681B2

Reaction notes

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