Acetic Anhydride → HCID 11998805, compound

HRID 1364103Notes

Reaction equation

HRID 1364103 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:26][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][C@@H:11]3[CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[S:9][C:5]=2[C:4](=[O:27])[CH2:3]1.C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:36]([N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([CH2:16][C@H:11]2[CH2:12][O:13][CH2:14][CH2:15][N:10]2[C:8]2[S:9][C:5]3[C:4](=[O:27])[CH2:3][C:2]([CH3:28])([CH3:1])[CH2:26][C:6]=3[N:7]=2)=[CH:18]1)(=[O:38])[CH3:37]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11998803HCID 11998803, compound

Product 1

HCID 11998805HCID 11998805, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of Example 25 (0.10 g, 0.25 mmol) in DCM (10 mL) was added triethylamine (0.03 g, 0.04 mL, 0.28 mmol), acetic anhydride (0.03 g, 0.03 mL, 0.30 mmol) and a catalytic amount of DMAP. The reaction mixture was stirred at r.t. for 16 h before being diluted with DCM (50 mL) and washed with sat. NaHCO3 solution (2×25 mL) and sat. brine (25 mL). The organic fraction was dried over MgSO4 and concentrated in vacuo. Purification by column chromatography (SiO2, 45:55 EtOAc/hexanes) gave the title compound (0.05 g, 49%) as a white solid. δH(CDCl3) 8.37 (1H, d, J 7.1 Hz), 7.82 (1H, dd, J 6.7 and 2.5 Hz), 7.32 (3H, m), 4.35 (1H, bs), 4.02 (1H, m), 3.82 (1H, d, J 11.9 Hz), 3.48-3.69 (4H, m), 3.31 (1H, m), 3.00 (1H, m), 2.66 (2H, d, J 3.3 Hz), 2.55 (3H, s), 2.34 (2H, s), 1.08 (6H, s). LCMS (ES+) 438.0 (M+H)+.

Workup

  1. washwashed with sat. NaHCO3 solution (2×25 mL) and sat. brine (25 mL)
  2. dry with materialThe organic fraction was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (SiO2, 45:55 EtOAc/hexanes)

Sources & evidence

ORD record
ord-dd1f077c1e584d338c55298dfdfc520d
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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