Acetic Anhydride → HCID 58236598, compound

HRID 1026822Notes

Reaction equation

HRID 1026822 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:30][C:31](=[O:46])[CH2:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([S:42]([CH3:45])(=[O:44])=[O:43])[CH:37]=2)=[O:34])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][NH:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:20][N:19]=3)[S:17][C:10]=12.[C:47](OC(=O)C)(=[O:49])[CH3:48]>>[F:1][C:2]1[CH:3]=[C:4]([NH:30][C:31](=[O:46])[CH2:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([S:42]([CH3:45])(=[O:43])=[O:44])[CH:37]=2)=[O:34])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:26][CH2:27][O:28][CH3:29])[C:47](=[O:49])[CH3:48])=[CH:20][N:19]=3)[S:17][C:10]=12

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 58236589HCID 58236589, compound

Product 1

HCID 58236598HCID 58236598, compoundYield 32.5%

Procedure

A solution of compound 345 (18.5 mg, 0.028 mmol) in acetic anhydride (1.31 ml, 13.9 mmol) was stirred at room temperature for 60 h. The solvent was removed under reduced pressure and the residue was triturated with water for 3 h. The solid suspension was filtered, the precipitate was rinsed with water and dried under high vacuum to afford compound 346 (6.4 mg, 9.07 μmol, 32.5%) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): mixture of rotamers, 10.64 (s, 1H), 10.60 (s, 1H), 8.55-8.49 (m, 2H), 8.38-8.21 (m, 3H), 7.91-7.86 (m, 2H), 7.78 (td, J=8.8, 2.0 Hz, 1H), 7.66-7.60 (m, 2H), 7.51 (t, J=8.8 Hz, 1H), 7.44 (dd, J=9.2, 1.6 Hz, 1H), 6.71-6.67 (m, 1H), 4.71 and 4.59 (2s, 2H), 3.58-3.23 (m, 14H), 3.21 (s, 3H), 2.13 and 2.05 (2s, 3H). MS (m/z): 706.5 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was triturated with water for 3 h
  3. filtrationThe solid suspension was filtered
  4. washthe precipitate was rinsed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-df2cf8bc6c3d41b2b173b0ee7bdf2da3
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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