Gamma-Butyrolactone → HCID 178520697, compound

HRID 351102Notes

Reaction equation

HRID 351102 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:12][C:13]([C:15]2[NH:16][CH:17]=[C:18]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][NH2:32])=[C:27]([Cl:33])[CH:26]=4)=[CH:23][NH:22][N:21]=3)[CH:19]=2)=[O:14])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8].[C:34]1(=[O:39])[O:38][CH2:37][CH2:36][CH2:35]1.C[Al](C)C>CS(C)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:12][C:13]([C:15]2[NH:16][CH:17]=[C:18]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][OH:39])=[C:27]([Cl:33])[CH:26]=4)=[CH:23][NH:22][N:21]=3)[CH:19]=2)=[O:14])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 7302Gamma-ButyrolactoneHCID 16682925TrimethylaluminumHCID 178509601HCID 178509601, compound

Product 1

HCID 178520697HCID 178520697, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl amine 11 (0.05 mmol) in DMSO (1 mL) was mixed with a solution of 4-butyrolactone (0.05 mmol) in CH2Cl2 (1 mL) under N2. To the mixture was added AlMe3 (0.25 mmol) and stirred for 10 min at room temperature and then 6 h at 45° C. The crude product was purified from preparatory HPLC to give II-8 as a yellow oil.

Workup

  1. custom6 h
  2. customat 45° C
  3. customThe crude product was purified from preparatory HPLC
  4. customto give II-8 as a yellow oil

Sources & evidence

ORD record
ord-ff491f292c6341ec86a4dc27503bde57
Source dataset
uspto-grants-2007_02
Patent number
US07183307B2

Reaction notes

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