Acetic Anhydride → HCID 69358968, compound

HRID 852613Notes

Reaction equation

HRID 852613 reaction equation
Cl.[O:2]=[S:3]1(=[O:22])[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][NH:13]2.CCN(CC)CC.[C:30](OC(=O)C)(=[O:32])[CH3:31]>CCOC(C)=O>[C:30]([N:13]1[C:14]2[C:10](=[C:9]([N:4]3[CH2:5][CH2:6][CH2:7][CH2:8][S:3]3(=[O:2])=[O:22])[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=2)[CH2:11][CH2:12]1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69358356HCID 69358356, compound

Product 1

HCID 69358968HCID 69358968, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-2,3-dihydro-1H-indole-6-carboxylate hydrochloride salt (D234) (350 mg, 1.0 mmol, 1 equiv) in AcOEt (5 ml) were added NEt3 (140 ml, 1.0 mmol, 1 equiv) and acetic anhydride (0.5 ml, 5.6 mmol, 5.6 equiv) and the resulting mixture was stirred at 50° C. for 30 min then cooled to room temperature and washed with a 2N aqueous HCl solution followed by a saturated aqueous NaHCO3 solution, then dried over MgSO4 and concentrated in vacuo to give methyl 1-acetyl-4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-2,3-dihydro-1H-indole-6-carboxylate (D235) as a white solid which was used in the next step without further purification. [M+H]+=353.2, RT=2.24 min.

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with a 2N aqueous HCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e79a4f447cf94f4f9a853018bcfa8a8a
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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