HCID 58109401, compound → HCID 58109295, compound

HRID 2037423Notes

Reaction equation

HRID 2037423 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:9]=[C:10]([CH3:29])[CH2:11][CH2:12][N:13]([C@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[OH:9][C:10]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:29])[CH2:11][CH2:12][N:13]([C@H:21]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:22])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 58109401HCID 58109401, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 58109295HCID 58109295, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phenylmagnesium bromide (1.0 M in THF, 1.0 mL) was added dropwise to a solution of (S)-tert-butyl 3-oxobutyl(1-phenylethyl)carbamate (0.0421 g, 0.144 mmol in THF (4 mL) under N2 at rt. After the solution was stirred for 14 h, the reaction was quenched with 10% aq Na2CO3 (0.5 mL) and diluted with CH2Cl2. The organic layer was dried over Na2SO4. After the solvents were evaporated, the crude product was directly used in the next step without further purification.

Workup

  1. customthe reaction was quenched with 10% aq Na2CO3 (0.5 mL)
  2. additiondiluted with CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customAfter the solvents were evaporated
  5. customthe crude product was directly used in the next step without further purification

Sources & evidence

ORD record
ord-29a6230d1ddb44429a5b0f4970db81e7
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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