Acetic Anhydride → HCID 54703350, compound

HRID 982866Notes

Reaction equation

HRID 982866 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]1[S:17][CH2:16][CH2:15][N:14]=[C:13]([C:18]2[C:19](=[O:26])[O:20][C:21]([CH3:25])=[CH:22][C:23]=2[OH:24])[CH2:12]1.[BH4-].[Na+].[C:29](OC(=O)C)(=[O:31])[CH3:30].CCN(C(C)C)C(C)C>C(#N)C.O.C(O)C>[C:29]([N:14]1[CH:13]([C:18]2[C:19](=[O:26])[O:20][C:21]([CH3:25])=[CH:22][C:23]=2[OH:24])[CH2:12][CH:11]([C:4]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=2[O:2][CH3:1])[S:17][CH2:16][CH2:15]1)(=[O:31])[CH3:30]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 1354004393-(7-(2,4-Dimethoxyphenyl)-2,3,6,7-tetrahydro-(1,4)thiazepin-5-yl)-4-hydroxy-6-methylpyran-2-one

Product 1

HCID 54703350HCID 54703350, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

3-[7-(2,4-Dimethoxyphenyl)-2,3,6,7-tetrahydro-[1,4]thiazepin-5-yl]-4-hydroxy-6-methyl-pyran-2-one (187 mg, 0.5 mmol), prepared as in Reference 5, was combined with absolute ethanol (5 mL) and sodium borohydride (20 mg, 0.526 mmol) and the mixture was warmed on a hot plate to form a solution. The progress of the reaction was followed by analytical HPLC and LCMS and when complete (5 hours) acetic anhydride (1.5 ml. 30 eq) and DIPEA (0.6 mmol, 0.1 mL) were added. The reaction was stirred at room temperature overnight. Product was isolated by preparative HPLC (RPC18 column, acetonitrile/water containing 0.1% HCl) to provide 3-[4-acetyl-7-(2,4-dimethoxy-phenyl)-[1,4]thiazepan-5-yl]-4-hydroxy-6-methyl-pyran-2-one (25 mg). LCMS: MH+ 420.2.

Workup

  1. temperaturethe mixture was warmed on a hot plate
  2. customto form a solution
  3. additionwere added

Sources & evidence

ORD record
ord-0220214a1cb04e3b9ce11bb9d8dce149
Source dataset
uspto-grants-2005_03
Patent number
US06861419B2

Reaction notes

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