Dimethylformamide → HCID 53730614, compound

HRID 2258033Notes

Reaction equation

HRID 2258033 reaction equation
[C:1]1([CH:7]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:8]([NH:10][CH:11]([CH:21]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)[S:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[C:12]([O:14]CC[Si](C)(C)C)=[O:13])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[C:39]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([NH:10][CH:11]([CH:21]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)[S:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[C:12]([OH:14])=[O:13])=[O:9])[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86751165HCID 86751165, compound

Product 1

HCID 53730614HCID 53730614, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.40 g (0.65 mmol) of (R,S; R,S)-2- diphenylacetylamino-3-(3-methoxyphenyl)-3-(3-methoxyphenyl-sulfanyl) propionic acid, 2-trimethylsilylethyl ester of Example 34, 3.3 mL of N,N-dimethylformamide and 3.3 mL (3.3 retool) of 1M tetrabutylammonium fluoride in tetrahydrofuran is stirred at room temperature for 30 minutes. Ethyl acetate (100 mL) is added and the solution is washed with 80 mL of 1N hydrochloric acid and 80 mL of brine, dried (magnesium sulfate) and evaporated to give the product; wt 0.31 g (92%). Recrystallization from ethyl acetate-heptane gives product as a 9:1 mixture of diastereomers by NMR and hplc;

Workup

  1. washthe solution is washed with 80 mL of 1N hydrochloric acid and 80 mL of brine
  2. dry with materialdried (magnesium sulfate)
  3. customevaporated
  4. customto give the product
  5. customRecrystallization from ethyl acetate-heptane
  6. customgives product
  7. additionas a 9:1 mixture of diastereomers by NMR and hplc

Sources & evidence

ORD record
ord-e8069374fc674a8186008382134cbc90
Source dataset
uspto-grants-1997_08
Patent number
US05658943

Reaction notes

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