Acetic Anhydride → HCID 53730221, compound

HRID 964323Notes

Reaction equation

HRID 964323 reaction equation
[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24](=[O:26])[NH2:25])[CH:17]=1)[CH:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:4]1[S:9][CH2:8][CH2:7][CH2:6][S:5]1.C(N(CC)CC)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>C1COCC1.CN(C1C=CN=CC=1)C>[C:34]([O:1][CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24](=[O:26])[NH2:25])[CH:17]=1)[CH:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:4]1[S:9][CH2:8][CH2:7][CH2:6][S:5]1)(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 54211372HCID 54211372, compound

Product 1

HCID 53730221HCID 53730221, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5 (192 mg, 0.5 mmol) in 10 mL THF was added DMAP (2 mg), triethylamine (70 mL, 0.5 mmol), and acetic anhydride (94 mL, 1.0 mmol). The solution was stirred at room temperature for 4 h, and then partitioned between ethyl acetate (50 mL) and 5% sodium bicarbonate (50 mL). The organic phase was washed with water (3 X 5 50 mL), dried with Mg2SO4, and evaporated to yield a colorless oil. Yield 205 mg (98%). IR: 3479, 3331 (br), 1747, 1694, 1589, 1 443, 1224, 1033, 910, 718 cm-1. 1H NMR (CDCl3, TMS) d 7.740 (dd, J=8.15, 1.55 Hz, 2 H), 7.348-7.281 (m, 3 H), 7.111 (t, J=7.96 Hz, 1 H), 6.801 (dd, J=8.18, 2.53 Hz, 1 H), 6.686 (d,J=7.59 Hz, 1 H), 6.521 (s, 2 H), 6.312 (s, 1 H), 6.136 (s, 1 H), 4.238 (s, 2 H), 2.751-2.597 (m, 4 H), 2.104 (s, 3 H), 1.933-1.857 (s, 1 H). 13C NMR (CDCl3, TMS) d 171.080, 169.318, 156.012, 136.974, 130.771, 128.402, 128.045, 127.738, 122.586, 115.072, 114.635, 79.890, 66.982, 63.133, 27.270, 27.109, 24.568, 20.848. Anal. Calcd. for C21H23NO4S2 : C, 60.41; 11, 5.55; N, 3.5. Found: C, 5 9.92; H, 5.76; N, 3.14.

Workup

  1. custompartitioned between ethyl acetate (50 mL) and 5% sodium bicarbonate (50 mL)
  2. washThe organic phase was washed with water (3 X 5 50 mL)
  3. dry with materialdried with Mg2SO4
  4. customevaporated
  5. customto yield a colorless oil

Sources & evidence

ORD record
ord-646be7ed74a641f99e082691e176e6b5
Source dataset
uspto-grants-1998_06
Patent number
US05767288

Reaction notes

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