Acetic Anhydride → HCID 23648638, compound

HRID 404905Notes

Reaction equation

HRID 404905 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[S:6][C:7]([C:10]2[CH:14]=[C:13]([CH:15]([NH2:17])[CH3:16])[O:12][N:11]=2)=[CH:8][N:9]=1.C(N(CC)CC)C.[C:31](OC(=O)C)(=[O:33])[CH3:32]>ClCCl>[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[S:6][C:7]([C:10]2[CH:14]=[C:13]([CH:15]([NH:17][C:31](=[O:33])[CH3:32])[CH3:16])[O:12][N:11]=2)=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69438003HCID 69438003, compound

Product 1

HCID 23648638HCID 23648638, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 37A (358 mg, 1.02 mmol) and triethylamine (426 μL, 3.06 mmol) in dichloromethane (5 mL) was added acetic anhydride (116 μl, 1.22 mmol) at ambient temperature. The reaction was stirred for 10 minutes and was then concentrated on a rotary evaporator. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 30% to 80% ethyl acetate in hexanes to give 338 mg (94%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.42 (d, J=7.35 Hz, 3H) 1.87 (s, 3H) 3.82 (s, 3H) 4.98-5.18 (m, 1H) 6.89 (s, 1H) 7.05 (dd, J=9.19, 2.94 Hz, 1H) 7.27 (d, J=2.94 Hz, 1H) 7.56 (d, J=9.19 Hz, 1H) 7.94 (s, 1H) 8.51 (d, J=7.72 Hz, 1H); MS (ESI) m/z 394.0 (M+H)+.

Workup

  1. concentrationwas then concentrated on a rotary evaporator
  2. customThe concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 30% to 80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-da337308b0c84852b68cdb23d4bb58a3
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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