Acetic Anhydride → HCID 53730221, compound

HRID 376782Notes

Reaction equation

HRID 376782 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 (±)-1-hydroxy-1-(3-carbamylmethoxyphenyl)-2-phenyl-2-(1,3-dithian-2-yl)-ethane (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 (3×50 mL), dried with Mg2SO4, and evaporated to yield a colorless oil. Yield 205 mg (98%). IR: 3479, 3331 (br), 1747, 1694, 1589, 1443, 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=7.59Hz, 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; H, 5.55; N, 3.35. Found: C, 59.92; 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 (3×50 mL)
  3. dry with materialdried with Mg2SO4
  4. customevaporated
  5. customto yield a colorless oil

Sources & evidence

ORD record
ord-2fd9b947bb2845a59f5c9836ffc1aabb
Source dataset
uspto-grants-2000_02
Patent number
US06022529

Reaction notes

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