Acetic Anhydride → HCID 178472731, compound

HRID 576567Notes

Reaction equation

HRID 576567 reaction equation
[CH2:1]([O:3][C:4](=[O:55])[CH2:5][N:6]([C:8](=[O:54])[C@@H:9]([NH:25][C:26](=[O:53])[C@@H:27]([NH2:52])[CH2:28][CH2:29][CH2:30][NH:31]/[C:32](/[NH2:51])=[N:33]\[S:34]([C:37]1[C:38]([CH3:50])=[C:39]([CH3:49])[C:40]2[O:44][C:43]([CH3:46])([CH3:45])[CH2:42][C:41]=2[C:47]=1[CH3:48])(=[O:36])=[O:35])[CH2:10][N:11]([CH3:24])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[CH3:7])[CH3:2].CCN(C(C)C)C(C)C.[CH3:65][C:66](OC(C)=O)=[O:67]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:55])[CH2:5][N:6]([C:8](=[O:54])[C@@H:9]([NH:25][C:26](=[O:53])[C@@H:27]([NH:52][C:66](=[O:67])[CH3:65])[CH2:28][CH2:29][CH2:30][NH:31]/[C:32](/[NH2:51])=[N:33]\[S:34]([C:37]1[C:38]([CH3:50])=[C:39]([CH3:49])[C:40]2[O:44][C:43]([CH3:45])([CH3:46])[CH2:42][C:41]=2[C:47]=1[CH3:48])(=[O:35])=[O:36])[CH2:10][N:11]([CH3:24])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 178472733HCID 178472733, compound

Product 1

HCID 178472731HCID 178472731, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of compound F (6.6 g, 7.8 mmol) in CHCl3 (50 mL) at 5° C. was added DIPEA (4.8 mL, 27.4 mmol) followed by Ac2O (0.9 mL, 9.4 mmol). The reaction mixture was stirred at ambient temperature for 30 min. Solvents were removed in vacuo, and then the residue was diluted with water (500 mL) and EtOAc (500 mL). The organic layer was separated and washed with water (300 mL), 2% aqueous H2SO4 (200 mL), water (2×300 mL) and brine (100 mL). The organic layer was separated, dried over Na2SO4 and solvent removed in vacuo to afford compound G (5.5 g, 82%). LC-MS [M+H] 853.4 (C36H52N8O12S2+H, calc: 853.9). Purity >95% (UV/254 nm). Compound G was used without further purification.

Workup

  1. customSolvents were removed in vacuo
  2. additionthe residue was diluted with water (500 mL) and EtOAc (500 mL)
  3. customThe organic layer was separated
  4. washwashed with water (300 mL), 2% aqueous H2SO4 (200 mL), water (2×300 mL) and brine (100 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4 and solvent
  7. customremoved in vacuo

Sources & evidence

ORD record
ord-14ecdb48409d48be889d61f396727d77
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

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