Dimethylformamide → 3-[(2S,3S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-fluorophenyl)-1-oxobutanyl]thiazolidine

HRID 970207Notes

Reaction equation

HRID 970207 reaction equation
[N:1]([C@@H:4]([C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH3:9])[C:5]([OH:7])=O)=[N+]=[N-].Cl.CN(C)CCCN=C=NCC.[OH:29][C:30]1[C:38]2N=NNC=2C=C[CH:31]=1.[S:39]1[CH2:43][CH2:42][NH:41][CH2:40]1.[CH3:44]CN(C(C)C)C(C)C.CN(C)[CH:55]=[O:56]>C(OCC)(=O)C>[C:30]([O:29][C:55]([NH:1][C@@H:4]([C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH3:9])[C:5]([N:41]1[CH2:42][CH2:43][S:39][CH2:40]1)=[O:7])=[O:56])([CH3:31])([CH3:38])[CH3:44]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 10444ThiazolidineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86605120(2S,3S)-2-Azido-3-(4-fluorophenyl)butanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 694229793-[(2S,3S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-fluorophenyl)-1-oxobutanyl]thiazolidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the product from Step D (0.19 g, 0.65 mmol) in anhydrous dimethylformamide (DMF, 2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.19 g, 0.99 mmol), hydroxybenzotriazole (HOBT, 0.13 g, 0.96 mmol), thiazolidine (0.26 mL, 3.3 mmol) and N,N′-diisopropylethylamine (0.33 mL, 1.9 mmol). After stirring at room temperature for 12 h, the reaction was diluted with ethyl acetate. The organic phase was washed sequentially with brine, 1N hydrochloric acid and 1N aqueous sodium hydroxide solution, dried over sodium sulfate, and evaporated in vacuo to yield the crude coupled product, which was used directly in the next step.

Workup

  1. washThe organic phase was washed sequentially with brine, 1N hydrochloric acid and 1N aqueous sodium hydroxide solution
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customto yield the crude

Sources & evidence

ORD record
ord-9e57c806683349efb7c4a76b49115741
Source dataset
uspto-grants-2007_12
Patent number
US07309714B2

Reaction notes

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