Triethylamine → HCID 15703817, compound

HRID 1534370Notes

Reaction equation

HRID 1534370 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH3:13][C:14]1[CH:19]=[C:18]([OH:20])[C:17]2[O:21][C:22]3[C:27]([C:28]([O:30][CH2:31][C:16]=2[CH:15]=1)=[O:29])=[C:26]([O:32][CH3:33])[C:25]([C@@H:34]([OH:39])[CH2:35][CH:36]([CH3:38])[CH3:37])=[CH:24][CH:23]=3>C(Cl)Cl>[OH:39][CH:34]([C:25]1[CH:24]=[CH:23][C:22]2[O:21][C:17]3[C:18]([O:20][S:9]([CH3:8])(=[O:11])=[O:10])=[CH:19][C:14]([CH3:13])=[CH:15][C:16]=3[CH2:31][O:30][C:28](=[O:29])[C:27]=2[C:26]=1[O:32][CH3:33])[CH2:35][CH:36]([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12421311-Hydroxy-3-(1-hydroxy-3-methylbutyl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one

Product 1

HCID 15703817HCID 15703817, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

0.14 ml (1.0 mmol) of triethylamine and 86 μl (1.1 mmol) of methanesulphonyl chloride are added at 0° C. under argon to 150 mg (0.4 mmol) of penicillide (Ib) in 3 ml of methylene chloride and the mixture is stirred at 25° C. for 12 h. Acidifying to pH 2, extracting with methylene chloride, washing, drying and evaporating yields, after chromatography on silica gel Si60 in ether/petroleum ether 2:1, 75 mg (41% of theory) of colorless solid

Workup

  1. extractionextracting with methylene chloride
  2. washwashing
  3. customdrying
  4. customevaporating
  5. customyields

Sources & evidence

ORD record
ord-2f1f570c44084a02831a9afb1b0ee960
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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