Hydrochloric Acid → HCID 11220404, compound

HRID 989898Notes

Reaction equation

HRID 989898 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:8][CH:9]=1)=[O:4].[Li+].[I-].Cl>N1C=CC=CC=1>[C:3]([C:5]1[N:6]=[C:7]([CH2:10][CH:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:8][CH:9]=1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 23389069Ethyl (+/-)-4-(4-methoxycarbonyl-1,3-oxazol-2-yl)-3-phenylbutanoate

Product 1

HCID 11220404HCID 11220404, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of ethyl (±)-4-(4-methoxycarbonyl-1,3-oxazol-2-yl)-3-phenylbutanoate (267 mg, 0.84 mmole) and LiI (338 mg, 2.52 mmole) in pyridine (5 mL) was heated to reflux. After 18 hr, the mixture was cooled to RT, poured into 10% HCl (150 mL), then extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated to give the title compound (205 mg, 80%) as a white solid: MS (ES) m/e 304 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5588958b415d4be39f7d8d9071022f4e
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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